Title:
【発明の名称】新規なオリゴ糖含有14‐アミノステロイド化合物および新規なジアステレオ選択的アミノステロイド法の化学
Document Type and Number:
Japanese Patent JPH09502982
Kind Code:
A
Abstract:
The present invention relates to oligosaccharide-containing 14-aminosteroid compounds and the pharmaceutically-acceptable acid salts or esters thereof of the general formula: wherein a) R1 is (i) COOR5, where R5 is hydrogen, a 1-6 carbon lower alkyl ; a 1-6 carbon lower alkyl substituted by an amino group; an arylalkyl or heteroarylalkyl or a carbocyclic ring, or (ii) CHR6OH, where R6 is a hydrogen atom or 1-6 carbon lower alkyl group, or (iii) COR''', where R''' is hydrogen; 1-6 carbon lower alkyl; 1-6 carbon lower alkyl substituted amino; amino or dialkylamino; and b) R2 is -NR7R8, where R7 and R8, which may be the same or different, are hydrogen atoms or a 1-6 carbon lower alkyl ; and c) R3 is (i) an oligosaccharide sugar residue having the following structure: where R9 is hydrogen; methyl; hydroxy; carboxy; acetoxy; arylalkyloxy; heteroarylalkyloxy or benzoxy; R10 is hydrogen; methyl; carboxy; acetoxy; arylalkyloxy; heteroarylalkyloxy; benzoxy or hydroxy; R11 is oxygen; wherein further when R11 is a substituent on the terminal monosaccharide sugar residue; R11 is OH; methyl; acetoxy; arylalkyloxy; heteroarylalkyloxy; and R12 is a hydrogen; methyl; methylhydroxymethyl; or acetoxymethyl; or (ii) an oligosaccharide sugar residue having the following structure: where R14 and R15, which may be the same or different, are hydrogen; 1-6 carbon lower alkyl; heteroarylalkyl; arylalkyl; heteroaryl or aryl; R17 can be hydrogen; hydroxy; acetoxy or benzoxy; R18 and R19 are hydroxy; acetoxy and benzoxy; or (iii) an oligosaccharide residue having the following structure: where R14 and R15, which may be the same or different, are hydrogen; 1-6 carbon lower alkyl; heteroaryl alkyl; arylalkyl; heteroaryl or aryl; R14a is oxygen; wherein further when R14a is a substituent on the terminal monosaccharide sugar residue; R14a must be hydroxy; methyl; acetoxy; arylalkyloxy or heteroarylalkyloxy; and d) R4 is (i) OH, or (ii) H, or (iii) OR13, where R13 is a monosaccharide sugar residue; acetoxy; benzoxy; arylalkyl or heteroarylalkyl; and e) Z is (i) -CH-, where a and b are single bonds, or (ii) =C, where either a or b is a double bond. The present invention also relates to a process for introducing an amino group at the 14-position on a steroid nucleus wherein said amino group is diasteroselectively introduced onto the 14-position of the steroid nucleus via an iodoisocyanate addition comprising the steps of: a) adding the iodoisocyanate to the 14-15 position double bond on the steroid nucleus; and b) dehalogenation; and c) isocyanate conversion to the amine moiety on the 14-position of the steroid nucleus.
Inventors:
Dibus, paul michael
Johnson, Roland Norman
Moose, Randy Stuart
Liu, Song
David Edward, Port Rock
Johnson, Roland Norman
Moose, Randy Stuart
Liu, Song
David Edward, Port Rock
Application Number:
JP50995294A
Publication Date:
March 25, 1997
Filing Date:
September 23, 1994
Export Citation:
Assignee:
THE PROCTER AND GAMBLE COMPANY
International Classes:
A61K31/7036; A61K31/704; A61P9/00; C07J3/00; C07J17/00; C07J19/00; C07J41/00; (IPC1-7): C07J41/00; A61K31/705
Attorney, Agent or Firm:
Kazuo Sato (3 others)