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    Prodn. of alpha-keto acids from carbonyl cpds. - by reaction with new phosphonium salts and hydrogenolysis
    1.
    发明专利
    Prodn. of alpha-keto acids from carbonyl cpds. - by reaction with new phosphonium salts and hydrogenolysis 未知

    公开(公告)号：DE4112629A1

    公开(公告)日：1991-10-31

    申请号：DE4112629

    申请日：1991-04-18

    Applicant: BASF AG

    Inventor： SCHMIDT RICHARD R PROF DR ,  FRICK WENDELIN DR

    IPC: C07F9/54

    Abstract: Phosphonium salts of formula (I) are new, where Ar = phenyl opt. substd. by nonionic gps.; X = halogen. Prodn. of alpha-keto acids of formula (II) is effected by (a) reacting a carbonyl cpd. of formula (III) with (I) in an inert solvent in the presence of a base, and (b) removing the arylmethyl gps. from the resulting alpha,beta-unsatd. ester of formula (IV) by hydrogenolysis. R1 and R2 = H or organic gps., opt. forming a ring. USE - (II) include cpds. useful as intermediates for bacterial lipopolysaccharides (see DE4112630), amino acids or heterocyclic pharmaceuticals or plant protection agents.

    New 3,4-epoxy:sphingosine derivs. - for use in tumour and immune therapy and to influence circulation, also as intermediates for ceramide(s) and glycosphingolipid(s)
    2.
    发明专利
    New 3,4-epoxy:sphingosine derivs. - for use in tumour and immune therapy and to influence circulation, also as intermediates for ceramide(s) and glycosphingolipid(s) 未知

    公开(公告)号：DE4025316A1

    公开(公告)日：1992-02-13

    申请号：DE4025316

    申请日：1990-08-09

    Applicant: BASF AG

    Inventor： SCHMIDT RICHARD R PROF DR ,  BIRK ROLF

    IPC: C07D303/36

    Abstract: Epoxy-sphingosine derivs. of formula (I) are new:. In (I) X = N3 or NH2. (I) are prepd. by: (a) Gringard alkylation of 2,4-0-benzylidene-D------ (8); (b) sepn. of the prods. into diastensomers (Ia) and (1b); (c) conversion of the 3-hydroxyl gp. into an azide deriv. (3) via a reactive ester (2); (d) contension of the pure hydroxyl gp. into a reactive ester (4); (e) removal of the benzylidene protecting gp. under acid conditions to give (5a); (f) formation of (I; X=N3) under basic conditions; and (g) opt. conversion of (I; X=N3) to (I;X=NH2) with triphenylphosphine in the presence of water. R=C8-16 H17-33; Pg=protecting gp. USE - (I) are useful as modulators of intercellular communication and thus in control of differentiation and proliferation, esp. of malignant cells. They may also be used as modulators of immune reactions and as controllers of coagulation. (I) are also useful as intermediates in the prepn. of ceramides and glycosphingolipids. Admin. is oral, buccel, parenterel or topical. Systemic admin. is e.g. 1-100mg/kg/day.

    (6R,7S,8R)-7,8-di:azido-6,9-di:silyl-oxy-nonanoate ester prepn. - by silylation of A 6,7,8,9-tetra:hydroxy-nonanoic acid ester followed by reaction with a sulphonic acid chloride and sodium azide
    4.
    发明专利
    (6R,7S,8R)-7,8-di:azido-6,9-di:silyl-oxy-nonanoate ester prepn. - by silylation of A 6,7,8,9-tetra:hydroxy-nonanoic acid ester followed by reaction with a sulphonic acid chloride and sodium azide 未知

    公开(公告)号：DE3933209A1

    公开(公告)日：1991-04-11

    申请号：DE3933209

    申请日：1989-10-05

    Applicant: BASF AG

    Inventor： SCHMIDT RICHARD R PROF DR ,  PLATSCHER MICHAEL DR

    IPC: C07D233/32 ,  C07F7/18

    Abstract: The prepn. of (6R,7S,8R)-7,9-diazido-6,9-disilyloxy-nonanoic acid ester of formula (I) comprises: (a) reacting a (6R,7S,8R), 6,7,8,9-tetrahydroxy-nonanoic acid ester of formula (II) with tert. butyl-dimethylsilyl chloride or thexyldimethylsilyl chloride in an inert solvent in the presence of a base; (b) reacting the (6R,7S,8R)-6,9-disilyloxy-7,8-dihydroxy-nonanoic acid ester of formula (III) formed with a sulphonic acid chloride of formula R3SO2Cl (IV) in pyridine, and (c) reacting the resulting (6R,7S,8R)-6,9-disilyl-oxy-7,8-disulphonyloxy-nonanoic acid ester of formula (V) with sodium azide in dimethylsulphoxide at 100-130 (esp. 115-125)deg.C. In formulae, R1 = 1=4C alkyl, R2 = tert. butyldimethylsilyl or thexyldimethylsilyl, and R3 = Me or p-tolyl. USE/ADVANTAGE - (I) are intermediates in the prepn. of (+)-biotin (vitamin H) which, as a co-factor of enzymes, plays a decisive role in biochemical processes in which carbonic acid is transferred or fixed. The process uses fewer reaction steps to produce (I) than previously. Starting from D-arabinose, it is possible to prepare (I) in only 10 synthesis steps - the shortest so far.

    New lipid deriv. modulators of glycosphingolipid biosynthesis - modulate intercellular communication, allowing control of proliferation in malignant cells
    5.
    发明专利
    New lipid deriv. modulators of glycosphingolipid biosynthesis - modulate intercellular communication, allowing control of proliferation in malignant cells 未知

    公开(公告)号：DE4025330A1

    公开(公告)日：1992-02-13

    申请号：DE4025330

    申请日：1990-08-09

    Applicant: BASF AG

    Inventor： SCHMIDT RICHARD R PROF DR ,  BAER THOMAS ,  SANDHOFF KONRAD PROF DR

    IPC: C07C215/24 ,  C07D203/10 ,  C07D295/125 ,  C07H15/10

    Abstract: Lipid derivs. of formula (I) are new. In (I) R1, R2 = H or Me; Y = H or an 8-22C acyl gp. opt. cong. 1-6 C=C double bonds; Z = OH, Me, SR3, N-pyrrolidinyl, N-piperidinyl, N-morpholinyl, 1-piperazinyl or N-thiomorpholinyl; or Y+Z = a bond; R3 = mono-or disaccharide; R4, R5=H or 1-4C alkyl; with the proviso that one of R1 and R2 is Me when Z is OH. Pref. R1 or R2 = Me; Y = H or satd. 13-22C acyl; Z=SR3 or NR4R5; or Y+Z=bond. USE - (I) are sphingolipid derivsl which are modulators and inhibitors of enzymatic glycosphingolipid biosynthesis, and may be inhibitors of protein kinase C. They may be used as modulators of intencellular communication and are thus important in treatment of oncological symptoms by controlling differentiation and proliferation of malignant cells. (I) may also be used as coagulation regulators and in modulation of immune reactions. (I) may be administered orally, buecally, parenterally or topically. Administration is 1-00mg/kg/day for system use. The use of (I) in the prepn. of non-natural glycosphingolipids is claimed.

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