公开(公告)号：NO130644B

公开(公告)日：1974-10-07

申请号：NO149169

申请日：1969-04-11

Applicant: HOECHST AG

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

IPC: A61K31/573 ,  A61K31/58 ,  C07C169/34

Abstract: DELTA 14-20-KETO-21-DIALKOXY STEROIDS ARE PREPARED BY OXIDIZING 20-KETO-15 alpha ,21-DIHYDROXY STEROIDS OF THE GENERAL FORMULA IN WHICH Y is an oxo group which may be ketalized, GROUP WHICH MAY BE ETHERIFIED OR ESTERIFIED, A DELTA 3-, DELTA 2-, OR DELTA 3,5-ENOL ETHER GROUP OR A DELTA 3-, DELTA 2-, OR DELTA 3,5-ENAMINO GROUP, WHICH GROUPS MAY HAVE A DOUBLE BOND IN THE 4-POSITION, AND IS A LOWER ACYCLIC OR CYCLIC ACETAL GROUPING, ACETALIZING THE 15 alpha -HYDROXY-20-KETO-21-OXO STEROIDS OBTAINED, REACTING THE 15 alpha -HYDROXY-20-KETO-21-DIALKOXY STEROIDS THUS OBTAINED WITH SULFONIC ACID HALIDES AND TREATING THE 15-SULFONIC ACID ESTERS THUS OBTAINED WITH AGENTS SPLITTING OFF ACIDS. The products are valuable intermediates for the manufacture of medicaments.

公开(公告)号：SE368570B

公开(公告)日：1974-07-08

申请号：SE1172170

申请日：1970-08-28

Applicant: HOECHST AG

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

IPC: A61K31/58 ,  A61K31/585 ,  A61K31/70 ,  A61K31/704 ,  A61P1/12 ,  A61P7/10 ,  A61P9/04 ,  C07J19/00 ,  C07C173/02

Abstract: 1323775 Cardial glycosides FARBWERKE HOECHST AG 1 Sept 1970 [29 Aug 1969(2)] 41722/70 Heading C2U The invention comprises compounds of formula where R is a steroid 3-yl radical of the 20(22)- cardenolide or 20,22-bufadienolide series; the two symbols R 1 together represent an epoxy group, or, when R is a cardenolide radical, they each may alternatively represent a hydrogen atom; R 2 is H or an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbyl or acyl group; and R 3 is H, Me or CH 2 OR 2 . Preparation of compounds (I) is from compounds of formula by catalytic hydrogenation (for products wherein R 1 = H) or by reaction with an organic peracid (for products wherein R 1 +R 1 = epoxy). Subsequently any 4 1 -acyloxy group may be hydrolysed, or any 4 1 -hydroxy group esterified or etherified. Digitoxigenin 3 - (# 2 - 2,3 - dideoxy - 4 - O- acetyl - D - arabinoside) is prepared by reacting digitoxigenin with di-O-acetyl-D-arabinal. The L-arabinoside isomer is prepared analogously and then hydrolysed to digitoxigenin 3-(# 2 - 2,3-dideoxy-L-arabinoside). Uzarigenin 3 - (# 2 - 2,3 - dideoxy - 4 - O- acetyl-α-L-rhamnoside) is prepared by reacting uzarigenin with di-O-acetyl-L-rhamnal. Other starting materials of Formula II are prepared as described in Specfications 1,268,230, 1,282,019 and 1,323,148. The steroids of Formula (I) are stated to possess cardiotonic, diuretic and antidiarrhoeal activities, and may be made up with carriers into pharmaceutical compositions for oral or parenteral administration.

公开(公告)号：ZA735149B

公开(公告)日：1974-06-26

申请号：ZA735149

申请日：1973-07-27

Applicant: HOECHST AG

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

IPC: C07J19/00 ,  A61K20060101 ,  A61K31/585 ,  A61P1/08 ,  A61P7/10 ,  A61P9/04 ,  A61P9/14 ,  C07C20060101 ,  C07D20060101 ,  C07J20060101 ,  C07C

Abstract: 1435204 Cardenolide glycosides HOECHST AG 30 July 1973 [29 July 1972] 36141/73 Heading C2U The invention comprises cardenolide 3-(2- deoxy-α-L-glycosides) of formula wherein R 1 is a steroid-3-yl radical of the 20(22)- cardenolide series; R 2 is H, C 1-5 aliphatic carboxylic acyl or C 7-8 aromatic carboxylic acyl; and R 3 is H, Me or OH 2 OR 2 . Preparation is from the corresponding 3-(2,3-dideoxy-2(3)-dehydro - α - L - glycosides) (cf. Specification 1,268,230) by hydroxybromination to give 3-(2- bromo - 2 - deoxy - α - L - glycosides), catalytic hydrogenation of which yields compounds I which may be interconverted by saponification or acylation within the sugar moiety. Digitoxigenin 3 - (2,3 - dideoxy - 2(3) - dehydro- α-L-rhamnoside)-4 1 -acetate is prepared from digitoxigenin by reaction with diacetyl-L- rhamnal. Compounds I are said to possesss cardiotonic, diuretic, antidiarrhoeal and venous tonusimproving properties, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.

公开(公告)号：DK128738B

公开(公告)日：1974-06-24

申请号：DK445070

申请日：1970-08-28

Applicant: HOECHST AG

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

IPC: A61K31/58 ,  A61K31/585 ,  A61K31/70 ,  A61K31/704 ,  A61P1/12 ,  A61P7/10 ,  A61P9/04 ,  C07J19/00 ,  C07C173/00

Abstract: 1323775 Cardial glycosides FARBWERKE HOECHST AG 1 Sept 1970 [29 Aug 1969(2)] 41722/70 Heading C2U The invention comprises compounds of formula where R is a steroid 3-yl radical of the 20(22)- cardenolide or 20,22-bufadienolide series; the two symbols R 1 together represent an epoxy group, or, when R is a cardenolide radical, they each may alternatively represent a hydrogen atom; R 2 is H or an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbyl or acyl group; and R 3 is H, Me or CH 2 OR 2 . Preparation of compounds (I) is from compounds of formula by catalytic hydrogenation (for products wherein R 1 = H) or by reaction with an organic peracid (for products wherein R 1 +R 1 = epoxy). Subsequently any 4 1 -acyloxy group may be hydrolysed, or any 4 1 -hydroxy group esterified or etherified. Digitoxigenin 3 - (# 2 - 2,3 - dideoxy - 4 - O- acetyl - D - arabinoside) is prepared by reacting digitoxigenin with di-O-acetyl-D-arabinal. The L-arabinoside isomer is prepared analogously and then hydrolysed to digitoxigenin 3-(# 2 - 2,3-dideoxy-L-arabinoside). Uzarigenin 3 - (# 2 - 2,3 - dideoxy - 4 - O- acetyl-α-L-rhamnoside) is prepared by reacting uzarigenin with di-O-acetyl-L-rhamnal. Other starting materials of Formula II are prepared as described in Specfications 1,268,230, 1,282,019 and 1,323,148. The steroids of Formula (I) are stated to possess cardiotonic, diuretic and antidiarrhoeal activities, and may be made up with carriers into pharmaceutical compositions for oral or parenteral administration.

公开(公告)号：DK128351B

公开(公告)日：1974-04-16

申请号：DK575770

申请日：1970-11-12

Applicant: HOECHST AG

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

IPC: C07J19/00 ,  B01J21/00 ,  B01J23/46 ,  B01J31/00 ,  C07D20060101 ,  C07J17/00 ,  C07C173/02

公开(公告)号：FI48075B

公开(公告)日：1974-02-28

申请号：FI96871

申请日：1971-04-06

Applicant: HOECHST AG

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

IPC: A61K31/70 ,  C07J71/00 ,  C07C173/04

Abstract: 1315235 Bufapolyenolides FARBWERKE HOECHST AG 19 April 1971 [8 April 1970] 26359/71 Heading C2U The novel compound 3#-(α-L-rhamnopyranosyloxy) - 14,15# - epoxy - 14# - bufa - 4,20,22- trienolide is prepared from proscillaridin by successively acylating the three sugar hydroxy groups, dehydrating in the 14,15-position, adding hypohalous acid acoross the resulting # 14 - double bond, dehydrohalogenating the resulting 14#-hydroxy-15α-halo grouping, and lastly liberating the three sugar hydroxy groups by saponification. The novel compound is stated to be cardioactive and may be made up with carriers into pharmaceutical compositions for oral administration.

公开(公告)号：SE363097B

公开(公告)日：1974-01-07

申请号：SE1172070

申请日：1970-08-28

Applicant: HOECHST AG

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

IPC: A61K31/585 ,  C07J19/00 ,  C07C173/02

公开(公告)号：DK127421B

公开(公告)日：1973-11-05

申请号：DK37072

申请日：1972-01-27

Applicant: HOECHST AG

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

IPC: A61K31/58 ,  A61K31/585 ,  A61K31/70 ,  A61K31/704 ,  A61P1/12 ,  A61P7/10 ,  A61P9/04 ,  C07J19/00 ,  C07C173/02

Abstract: 1323775 Cardial glycosides FARBWERKE HOECHST AG 1 Sept 1970 [29 Aug 1969(2)] 41722/70 Heading C2U The invention comprises compounds of formula where R is a steroid 3-yl radical of the 20(22)- cardenolide or 20,22-bufadienolide series; the two symbols R 1 together represent an epoxy group, or, when R is a cardenolide radical, they each may alternatively represent a hydrogen atom; R 2 is H or an aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbyl or acyl group; and R 3 is H, Me or CH 2 OR 2 . Preparation of compounds (I) is from compounds of formula by catalytic hydrogenation (for products wherein R 1 = H) or by reaction with an organic peracid (for products wherein R 1 +R 1 = epoxy). Subsequently any 4 1 -acyloxy group may be hydrolysed, or any 4 1 -hydroxy group esterified or etherified. Digitoxigenin 3 - (# 2 - 2,3 - dideoxy - 4 - O- acetyl - D - arabinoside) is prepared by reacting digitoxigenin with di-O-acetyl-D-arabinal. The L-arabinoside isomer is prepared analogously and then hydrolysed to digitoxigenin 3-(# 2 - 2,3-dideoxy-L-arabinoside). Uzarigenin 3 - (# 2 - 2,3 - dideoxy - 4 - O- acetyl-α-L-rhamnoside) is prepared by reacting uzarigenin with di-O-acetyl-L-rhamnal. Other starting materials of Formula II are prepared as described in Specfications 1,268,230, 1,282,019 and 1,323,148. The steroids of Formula (I) are stated to possess cardiotonic, diuretic and antidiarrhoeal activities, and may be made up with carriers into pharmaceutical compositions for oral or parenteral administration.

公开(公告)号：DK127110B

公开(公告)日：1973-09-24

申请号：DK29671

申请日：1971-01-22

Applicant: HOECHST AG

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

IPC: A61K31/585 ,  C07D20060101 ,  C07J19/00 ,  C07C173/02

Abstract: 1327745 4 - Chlorocardenolide glycosides FARBWERKE HOECHST AG 19 Jan 1971 [26 Jan 1970] 2585/71 Heading C2U The invention comprises compounds of formula (wherein R is an unsubstituted glycopyranosyl radical and R 1 is α-H, #-H or #-OH), and their preparation from the corresponding 3-ols by reaction with an acylated 1-halo-1-deoxyglycopyranose in the presence of silver carbonate and an inert solvent (with azeotropic distillation to remove the water of reaction) followed by hydrolysis of the acyl groups). 3#-Hydroxy - 4 - chloro - 14α - carda - 4,20(22)- dienolide is prepared from 3-oxo-14α-carda- 4,20(22)-dienolide via 3-oxo-4-chloro-14α-carda- 4,20(22)-dienolide. The 14#-isomer is prepared likewise. The inventive compounds are said to be cardioactive, and may be made up with carriers into pharmaceutical compositions for oral and parenteral administration.

公开(公告)号：DK126190B

公开(公告)日：1973-06-18

申请号：DK243470

申请日：1970-05-13

Applicant: HOECHST AG

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

IPC: A41D27/20 ,  A61K31/585 ,  C07J19/00 ,  C07C173/02

Abstract: 1308656 4-Chloro-carda-4,20(22)-dienolides FARBWERKE HOECHST AG 14 May 1970 [14 May 1969] 23473/70 Heading C2U The invention comprises 3-oxo-4-chloro-14#- hydroxycarda-4,20(22)-dienolide (V) and 3α,14#- or 3#,14#-dihydroxy -4 - chlorocarda - 4,20(22)- dienolide (VI), and their derivatives wherein one or more of the 1, 2, 6, 7, 11, 12 and 16- positions is substituted by an alkyl, acyl, C 1-3 acyloxy or ketalized oxo group. Preparation of the above is by the route: 3 - oxo - carda - 4,14,20(22) - trienolide # 3 - oxo - 4,14,15 - trichlorocarda - 4,20(22)- dienolide # 3 - oxo - 4 - chlorocarda - 4,14,20- (22) - trienolide # 3 - oxo - 4 - chloro - 14#- hydroxy - 15α - bromocarda - 4,20(22) - dienolide # V # VI. Pharmaceutical compositions comprise an inventive compound and a carrier. Compound V and its derivatives are said to be cardioactive, but no activity is specified for compound VI and its derivatives. Routes of administration are not specified.