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    Cardio-active glycosides of 3beta,14-dihydroxy - 4,5beta - oxido - 14beta - bufa - 20,22-dienolides and process for their preparation
    1.
    发明授权
    Cardio-active glycosides of 3beta,14-dihydroxy - 4,5beta - oxido - 14beta - bufa - 20,22-dienolides and process for their preparation 失效
    3BETA，14-二羟基-4,5BETA-OXIDO-14BETA-BUFA-20,22-二醇的制备活性糖苷及其制备方法

    公开(公告)号：US3741956A

    公开(公告)日：1973-06-26

    申请号：US3741956D

    申请日：1971-04-29

    Applicant: HOECHST AG

    Inventor： RADSCHEIT K ,  STACHE U ,  LINDNER E ,  FRITSCH W ,  HAEDE W

    IPC: A61K31/58 ,  A61K31/585 ,  C07J19/00 ,  C07J71/00 ,  C07C173/00

    CPC classification number: A61K31/58 ,  A61K31/585 ,  C07J19/00 ,  C07J71/00

    Abstract: IN WHICH R1 IS CH3-, CHO-, CH2OH, CH2O-ALKYL, CH2O ACYL AND R2 IS MONO-, DI- OR TRISACCHARIDYL, OPTIONALLY ESTERIFIED, ETHERIFIED OR CONDENSED WITH CARBONYL COMPOUNDS, E.G. 3B,14 - DIHYDROXY-4,5B-OXIDO-14B-BUFA20,22-DIENOLIDE, 3B-(A-L-RHAMNOSIDE) AND 3B,14-DIHYDROXY - 4,5B-OXIDO-14B-BUFA-20,22-DIENOLIDE, 3B-(B-D-GLUCOSIDE). METHOD FOR MAKING THESE COMPOUNDS (1) BY ACYLATING THE CORRESPONDING GLYCOSIDES, REACTING THE ACYLATES WITH HOHAL-FORMING AGENTS TO THE CORRESPONDING 4,5-HALOHYDRINS WHICH ARE THEN CONVERTED INTO 4,5B-EPOXIDES BY SPLITTING OFF HYDROGEN HALIDE, OF (2) BY REACTING THE CORRESPONDING AGLYCONES OF THE ABOVE FORMULA (R2"H) WITH ACYLATED 1-HALOPYRANOSES IN INERT SOLVENTS IN THE PRESENCE OF SILVER SALTS, AND FINALLY HYDROLYZING THE ACYLATED COMPOUNDS TO YIELD THE FREE GLYCOSIDES. THESE COMPOUNDS HAVE STRONG POSITIVE INOTROPIC ACTION AND A PRONOUNCED CARDIOACTIVE EFFICACY.

    ESTRANE

    17-(2-(O=)PYRAN-5-YL),14-HO,10-R1,4,5-(-O-),3-(R2-O-)-

    3-HYDROXY-4,5B-OXIDO - BUFADIENOLIDES OF THE GENERAL FORMULA

    3-amino-4,5-dehydro-cardenolides and process for their manufacture
    2.
    发明授权
    3-amino-4,5-dehydro-cardenolides and process for their manufacture 失效
    3-氨基-4,5-脱氢半胱氨酸及其制备方法

    公开(公告)号：US3801570A

    公开(公告)日：1974-04-02

    申请号：US3801570D

    申请日：1971-10-27

    Applicant: HOECHST AG

    Inventor： HAEDE W ,  RADSCHEIT K ,  STACHE U ,  FRITSCH W ,  LINDNER E

    IPC: A61K20060101 ,  A61K31/585 ,  C07C20060101 ,  C07D20060101 ,  C07J17/00 ,  C07J41/00 ,  C07C173/02

    CPC classification number: C07J19/00

    Abstract: 3-AMINO - 4,5 - DEHYDRO-CARDENOLIDES OF THE GENERAL FORMULA

    1-R7,3-(R1-NH-),11-R8,12-R5,14-R2,15-R3,16-R4,17-(5-(O=)-

    2,5-DIHYDROFUR-3-YL),19-R6-ANDROST-4-ENE

    IN WHICH R1 REPRESENTS HYDROGEN OR A LOWER ALIPHATIC ACYL RADICAL, R2 AND R3 EACH REPRESENT HYDROGEN OR HYDROXY, OR R2 AND R3 TOGETHER REPRESENT A FURTHER C-C BOND OR AN A- OR B-OXIDO GROUP, R4, R5, R6 AND R7 EACH REPRESENT HYDROGEN OR A HYDROXY GROUP WHICH MAY BE ESTERIFIEDTHE OH GROUP FOR R6 MAY ALSO BE ETHERIFIED-R8 REPRESENTS HYDROGEN OR HYDROXY, AND THE SALTS THEREOF WITH INORGANIC OR ORGANIC ACIDS, IF R1 REPRESENTS HYDROGEN. THE COMPOUNDS HAVE VALUABLE PHARMALOGICAL PROPERTIES, ESPECIALLY A POSITIVE OR NEGATIVE INOTROPIC ACTION AND A SUBSTANTIALLY INPROVED LIPID SOLUBILITY. METHODS FOR MAKING AND USING THE COMPOUNDS.

    Process for the manufacture of beta-(3-oxo-7alpha-acetylthio-17beta-hydroxy-4-androsten-17alpha-yl)-propionic acid gamma-lactone
    4.
    发明授权
    Process for the manufacture of beta-(3-oxo-7alpha-acetylthio-17beta-hydroxy-4-androsten-17alpha-yl)-propionic acid gamma-lactone 失效
    制备BETA（3-氧代-7α-乙酰基-17β-羟基-4-雄甾-4-烯-1-羧酸）丙酸乳酸 - 乳酸的方法

    公开(公告)号：US3847906A

    公开(公告)日：1974-11-12

    申请号：US40304073

    申请日：1973-10-03

    Applicant: HOECHST AG

    Inventor： RADSCHEIT K ,  STACHE U ,  BRODERSEN R

    IPC: C07J31/00 ,  C07J21/00 ,  C07C173/00

    CPC classification number: C07J21/00

    Abstract: 1. A PROCESS FOR THE MANUFACTURE OF B-(3-OXO-7-ACETYLTHIO-17B-HYDROXY-4-ANDROSTEN-17A-YL)-PROPIONIC ACID YLACTONE, WHICH COMPRISES OXIDIZING B-(3B,17B-DIHYDROXY-5ANDROSTEN-17A-YL)-PROPIONALDEHYDE ETHYLENE ACETAL ACCORDING TO THE OPPENAUER METHOD, DEHYDROGENATING THE B-(3OXO-17B-HYDROXY-4-ANDROSTEN-17A-YL)-PROPIONALDEHYDE ETHYLENE ACETAL OBTAINED WITH CHLORANIL IN METHANOL WITH SIMULTANEOUS CYCLIZATION, REACTING THE B-(3-OXO-17B-HYDROXY-4,6-ANDROSTADIEN-17''A-YL)-PROPIONALDEHYDE CYCLOHEMIHEMIACETAL METHYL GLYCOSIDE THUS OBTAINED WITH THIO-ACETIC ACID AND OXIDIZING THE 3-(3''-OXO-7''A-THIO-ACETYL-17''B-HYDROXY-4''-ANDROSTEN-17''A-YL)-PROPIONALDEHYDE CYCLOHEMIACETAL 1-THIOACETATE WITH CHROMIC TO YIELD THE CORRESPONDING Y-LACTONE.

    3beta-hydroxy-5alpha-cardenolides and-bufadienolides and process for their manufacture
    5.
    发明授权
    3beta-hydroxy-5alpha-cardenolides and-bufadienolides and process for their manufacture 失效
    3BETA-HYDROXY-5ALPHA-CARDENOLIDES AND-BUFADIENOLIDES AND PROCESS FOR MANTRIFACTURE

    公开(公告)号：US3812106A

    公开(公告)日：1974-05-21

    申请号：US16022071

    申请日：1971-07-06

    Applicant: HOECHST AG

    Inventor： STACHE U ,  RADSCHEIT K ,  FRITSCH W ,  HAEDE W

    IPC: C07D20060101 ,  C07J19/00 ,  C07C173/02 ,  C07C173/04

    CPC classification number: C07J75/00

    Abstract: A PROCESS FOR THE MANUFACTURE OF 3B-HYDROXY-5A-CARDENOLIDES AND 3B-HYDROXY-5A-BUTADIENOLIDES OF THE GENERAL FORMULA I

    10-R2,11-R6,12-R5,14-R3,15-R4,17-R1-ESTRAN-3-OL

    IN WHICH R1 REPRESENTS THE BUTENOLIDE RING OR THE A-OYRONE RING

    5-(O=)-2,5-DIHYDROFUR-3-YL OR

    6-(O=)-6H-PYRAN-3-YL

    R2 REPRESENTS CH3, CH2OH OR -CH2-OOC-CH3; R3 REPRESENTS A HYDROGEN ATOM IN A- OR B-POSITION OR A HYDROXY GROUP WHICH MAY BE ESTERIFIED; R4 REPRESENTS A HYDROGEN ATOM; OR R3 AND R4 TOGETHER REPRESENT A 14(15)DOUBLE BOND OR AN EPOXY GROUP IN 14,15B- OR 14,15A-POSITION; R5 AND R6 EACH REPRESENTS A HYDROGEN ATOM OR A HYDROXY GROUP IN A- OR B-POSITION WHICH MAY BE ESTERIFIED, WHICH PROCESS COMPRISES REDUCING 3-OXO-4(5)-DEHYDRO-CARDENOLIDES OR -BUFADIENOLIDES OF THE GENERAL FORMULA

    10-R2,11-R6,12-R5,14-R3,15-R4,17-R1-ESTR-4-EN-3-ONE

    IN WHICH R1, R2, R3, R4, R5 AND R6 HAVE THE MEANINGS GIVEN ABOVE AND R2 MAY ADDITIONALLY REPRESENT THE ALDEHYDE GROUP CHO, AND R5 AND R6 MAY REPRESENT THE OXO GROUP, WITH ORGANOMETALLIC REDUCING AGENTS OR REDUCING AGENTS HAVING A SIMILAR EFFECT, THE REDUCING POWER OF WHICH ARE SUPERIOR TO THAT OF SODIUM BORON HYDRIDE, IN THE PRESENCE OF ORGANIC NITROGEN BASES AT TEMPERATURES OF FROM -30* TO +60*C. CARDIOACTIVE 3B-HYDROXY-5A-CARDENOLIDES AND BUFADIENOLIDES OBTAINED BY THIS PROCESS.

    Process for the preparation of 14-anhydrobufaline
    6.
    发明授权
    Process for the preparation of 14-anhydrobufaline 失效
    制备14-ANHYDROBUFALINE的方法

    公开(公告)号：US3753980A

    公开(公告)日：1973-08-21

    申请号：US3753980D

    申请日：1971-10-29

    Applicant: HOECHST AG

    Inventor： HAEDE W ,  FRITSCH W ,  RADSCHEIT K ,  STACHE U

    IPC: C07J19/00 ,  C07C

    CPC classification number: C07J19/00

    Abstract: A PROCESS FOR THE PREPARATION OF 14-ANHYDROBUFALINE BY HYDROGENATING CATALYTICALLY 3-KETO-21-HYDROXY-$4,14,20CHOLATRIENIC ACID 21-LACTONE TREATING 3-KETO-21-HYDROXY5B-CHLOA-14,20-DIENE ACID-21-LACTONE OBTAINED WITH ELEMENTARY SULFUR IN AN INERT HIGH-BOILING SOLVENT AND REDUCING THE ANHYDROBUFALONE BY MEANS OF TRIMETHYL PHOSPHITE IN ISOPROPANOL IN THE PRESENCE OF IRIDIUM-IV-HYDROCHLORIC ACID.

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