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    PRODUCTION OF KETENIMINE
    1.
    发明专利
    PRODUCTION OF KETENIMINE 失效

    公开(公告)号：JP2001058977A

    公开(公告)日：2001-03-06

    申请号：JP23299999

    申请日：1999-08-19

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： SHIMIZU MASAO ,  SHIBUYA ISAO ,  GAMA YASUO

    IPC: C07C249/02 ,  C07C251/10 ,  C07C251/16

    Abstract: PROBLEM TO BE SOLVED: To obtain a ketenimine in a high yield under a mild condition without causing the environmental pollution problem by reacting a thioamide compound with a haloiminium salt. SOLUTION: The objective compound of formula III (e.g. N- benzylphenylketenimine) is obtained by desulfhydrating reaction of a compound of formula I (R1 and R2 are each H, an alkyl or an aryl; R3 is an alkyl or an aryl with proviso that the case of R1, R2 and R3 of all an aryl is omitted), e.g. phenylacetic acid thioanilide with a compound of formula II (R4 and R5 are each a lower alkyl; X is a halogen; Y is a counter anion; n is 0 or 1), e.g. 2-chloro-1,3-dimethylimidazolinium chloride. The above reaction is preferably carried out in a reactive solvent (e.g. methylene chloride) in the presence of a base (e.g. triethylamine or the like).

    DERIVATIVE OF 1,2-BENZISOTHIAZOLIN-3-ONE AND ITS PREPARATION
    2.
    发明专利
    DERIVATIVE OF 1,2-BENZISOTHIAZOLIN-3-ONE AND ITS PREPARATION 失效

    公开(公告)号：JP2001019683A

    公开(公告)日：2001-01-23

    申请号：JP19549199

    申请日：1999-07-09

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： SHIMIZU MASAO ,  SHIBUYA ISAO ,  GAMA YASUO ,  SHIBAUE MOTONARI ,  TAKAGI TOSHIYUKI

    IPC: C07D275/04

    Abstract: PROBLEM TO BE SOLVED: To obtain in safety and good yield the subject derivative of 1,2- benzothiazolin-3-one having various bioactivities without using a toxic gas by heating a sulfenamide compound. SOLUTION: The objective derivative of formula II (e.g. 1,2-benzisothiazolin-3- one, etc., of formula III) is obtained by carrying out a cyclization reaction of a sulfenamide compound of formula I [R1-R4 are each H, an alkyl, an alkoxy, etc.; R5 is a (substituted)alkyl, a cycloalkyl, etc.], (e.g. methyl 2- sulfenamoylbenzoate, etc.). The reaction is preferably carried out in the presence of a solvent (e.g. toluene, etc.), at 50-150 deg.C, for 2-8 hours.

    PRODUCTION OF BETA-GLUCOSIDE
    4.
    发明专利
    PRODUCTION OF BETA-GLUCOSIDE 失效

    公开(公告)号：JPH0570473A

    公开(公告)日：1993-03-23

    申请号：JP25974691

    申请日：1991-09-11

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： SASAKI MAKOTO ,  GAMA YASUO ,  ISHIGAMI YUTAKA ,  NAKANISHI HIROSHI

    IPC: C07H1/00 ,  C07H15/04 ,  C07H15/18 ,  C07H15/203

    Abstract: PURPOSE:To synthesize the title compound in high stereoselectivity without utilizing participation of adjacent group located at second position by reacting phenylthioglycoside with alcohols in the presence of a specific compound in a nitrile based solvent. CONSTITUTION:Phenylthioglycoside is reacted with alcohols (e.g. methanol, galactose, cholesterol or serine in the presence of a N-halosuccinic acid imide (preferably N-bromosuccinic acid imide) and trifluoromethanesulfonic acid in a nitrile-based solvent (e.g. acetonitrile or propionitrile), preferably at -78 to -42 deg.C for 0.5-1hr to provide the objective compound.

    NOVEL GLYCOSYLATION METHOD
    6.
    发明专利
    NOVEL GLYCOSYLATION METHOD 失效

    公开(公告)号：JPH03264595A

    公开(公告)日：1991-11-25

    申请号：JP6206690

    申请日：1990-03-13

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： SASAKI MAKOTO ,  GAMA YASUO ,  YASUMOTO MASAHIKO ,  ISHIGAMI YUTAKA

    IPC: C07H1/00 ,  C07H15/04 ,  C07H15/18 ,  C07H15/203 ,  C07J17/00

    Abstract: PURPOSE:To simply, safely, economically and highly selectively prepare a glycosylated compound by reacting a halogenated saccharide derivative with an alcohol in the presence of a tertial amine under a high pressure. CONSTITUTION:1.2-1.5 Equivalent (based on an alcohol) of a halogenated saccharide derivative (OH and amino groups are preliminarily protected with protecting groups) such as glucopyranosyl bromide, the alcohol such as methanol and molecular sieve 4A are dissolved in a solvent such as methylene chloride, sealed in a Teflon capsule, set in a high pressure reactor and subsequently subjected to a reaction at room temperature to 40 deg.C for 20-40 hours under >=4000 atmospheric pressure to form the objective glycosylation product, which is recrystallized, etc.

    PH-SENSITIVE LIPOSOME
    7.
    发明专利
    PH-SENSITIVE LIPOSOME 失效

    公开(公告)号：JPH03112924A

    公开(公告)日：1991-05-14

    申请号：JP24948589

    申请日：1989-09-26

    Applicant: AGENCY IND SCIENCE TECHN ,  LINTEC CORP

    Inventor： GAMA YASUO ,  ISHIGAMI YUTAKA ,  OKABE HIDEAKI ,  KAMAGAMI SABURO ,  KAIZE HISAYASU

    IPC: A61K8/11 ,  A61K8/00 ,  A61K8/14 ,  A61K8/44 ,  A61K8/49 ,  A61K9/127 ,  A61K47/18 ,  A61Q13/00 ,  B01J13/02

    Abstract: PURPOSE:To obtain a pH-sensitive liposome, containing N-acylhomoserine and/or N-acylhomoserine lactone in a wall membrane and capable of controlling release of a drug in response to a change in pH. CONSTITUTION:A pH-sensitive liposome containing 5-30%, preferably 10-20% N-acylhomoserine and/or N-acylhomoserine lactone (the acyl group is preferably derived from a 10-18C saturated or unsaturated fatty acid) in a wall membrane of a liposome. The aforementioned liposome has high biological stability and is stable in the same manner as that of a liposome composed of the standard material, chemically and colloidally stable for a long period without releasing an enclosed drug in preservation thereof at pH =6 of environment in the outer aqueous phase of the liposome and increasing the release rate as the pH value attains 7-8.

    METAL SOAP
    9.
    发明专利
    METAL SOAP 失效

    公开(公告)号：JPH01304034A

    公开(公告)日：1989-12-07

    申请号：JP13372188

    申请日：1988-05-30

    Applicant: AGENCY IND SCIENCE TECHN ,  IWATA KAGAKU KOGYO

    Inventor： ISHIGAMI YUTAKA ,  GAMA YASUO ,  TERADA MIYAJI ,  NAKAMURA HIROSHI

    IPC: C09K3/00 ,  B01F17/56 ,  C07H13/06 ,  C07H15/04 ,  C12N1/00 ,  C12P19/44

    Abstract: PURPOSE:To obtain a biological surfactant derived from a microorganism and made adaptable to a living body and showing specific compatibility in the living body, by reacting an aqueous solution of a multivalent metal salt with a sodium salt of rhamnolipid A or B. CONSTITUTION:Rhamnolipid is one kind of glycolipids and has such a structure that a hydrophilic group consists of a rhamnose residue and a carboxyl group, and an oleophilic group is composed of a two-chain alkyl group divided broadly into a decenoyl group and a structure wherein two hepthyl groups are branched from beta-hydroxypropionyl propionate. A sodium salt of rhamnolipid A (general formula I, M is a multivalent metal ion) or B (general formula II) and a salt of a multivalent metal such as calcium is reacted with said sodium salt to obtain metal soap. This metal soap is suitable for stable solubilization or emulsification to water and an org. solvent and has safety and biodegradability and can be widely utilized in fields of cosmetics and drugs.

    NOVEL N-GLYCOSIDE AND ITS PRODUCTION
    10.
    发明专利
    NOVEL N-GLYCOSIDE AND ITS PRODUCTION 失效

    公开(公告)号：JP2000072792A

    公开(公告)日：2000-03-07

    申请号：JP24390898

    申请日：1998-08-28

    Applicant: AGENCY IND SCIENCE TECHN

    Inventor： GAMA YASUO ,  SHIBUYA ISAO ,  SHIMIZU MASAO

    IPC: C07H19/12

    Abstract: PROBLEM TO BE SOLVED: To obtain the subject novel N-glycoside that is useful as a physiologically active compound or its intermediate compound from a readily available raw material. SOLUTION: This novel compound is an N-glycoside represented by formula I (Z is 2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyl; R1 and R2 are each an alkyl, an aryl, an aralkyl or the like), typically 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6- diethylamino-1,3,5-triazine-2,4-dione. The compound of formula I is readily prepared in high yield, for example, by allowing silver cyanate to react with an N-glycosyl-N',N'-disubstituted thiourea represented by formula II (Z1 is 2,3,4,6- tetra-O-acetyl-β-D-glucopyranosyl). The compound of formula I is useful as an intermediate for fine chemical products as medicines, agrochemicals and the like or as a physiologically active substance.

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