C - Chemistry – Metallurgy – 07 – F
Patent
C - Chemistry, Metallurgy
07
F
C07F 9/30 (2006.01) A61K 31/662 (2006.01) A61K 31/663 (2006.01) A61K 31/665 (2006.01) A61K 31/67 (2006.01) A61P 25/00 (2006.01) C07F 9/38 (2006.01) C07F 9/6527 (2006.01) C07F 9/655 (2006.01) C07F 9/6553 (2006.01)
Patent
CA 2626435
Hypophosphorous acid derivatives having Formula (I) wherein . M is a [C(R3,R4)]n1 - C(E,COOR1, N(H, Z)) group, or an optionally substituted Ar- CH(COOR1, N(H, Z)) group, or an a, ~, or a ~, g-cyclic aminoacid; . R1 is H or R, R being an hydroxy or a carboxy protecting group; . Z is H or an amino protecting group R', benzyl oxycarbonyl, benzyl or benzyl substituted; . E is H or a C1-C3 alkyl, aryl, an hydrophobic group; . R2 is selected in the group comprising: D-CH(R6)- C-(R7, R8), (R11,R12)CH- C(R9, R10), D - CH(OH), D- [C(R13, R14)]n3 -, C[(R15, R16, R17)]n4, D-CH2, (R18)CH = C(R19), D-(M1)n6-CO, Formula (II), PO(OH)2-CH2 or (PO(OH)2-CH2), (COOH-CH2)-CH2, with - D = H, OH, OR, (CH2)n2OH, (CH2)n1OR, COOH, COOR, (CH2)n2COOH, (CH2)n1COOR, SR, S(OR), SO2R, NO2, heteroaryl, C1-C3 alkyl, cycloalkyl, heterocycloalkyl, (CH2)n2- alkyl, (COOH, NH2)-(CH2)u1-cyclopropyl-(CH2)u2-, CO-NH-alkyl, Ar, (CH2)n2-Ar, CO-NH-Ar; - R3 to R19 being H, OH, OR, (CH2)n2OH, (CH2)n1OR, COOH, COOR, (CH2)n2COOH, (CH2)n1COOR, C1-C3 alkyl, cycloalkyl, (CH2)n1-alkyl, aryl, (CH2)n1-aryl, halogen, CF3, SO3H, (CH2)x PO3H2, with x = 0, 1 or 2, B(OH)2 , Formula (III), NO2 , SO2NH2 , SO2NHR; SR, S(O)R, SO2R, benzyl; - M1 is an alkylene or arylene group; - n1= 1, 2 or 3, n2= 1, 2 or 3, n3= 0, 1, 2 or 3 and n4= 1, 2 or 3, n5= 1,2 or 3, n6= 0 or 1, u1 and u2, identical or different = 0,1 or 2, with the proviso that Formula (I) does not represent the racemic (3R, S) and the enantiomeric form (3R) of 3 amino,3-carboxy-propyl-2'-carboxy- ethylphosphinic acid; 3 amino,3-carboxy-propyl- 4'carboxy,2'carboxy- butanoylphosphinic acid; 3 amino,3-carboxy-propyl- 2'carboxy- butanoylphosphinic acid; 3 amino,3-carboxy-propyl- 3'amino, 3'carboxy- propylylphosphinic acid; and 3 amino,3-carboxypropyl -7'amino-2', 7'- dicarboxyheptylphosphinic acid, said hypophosphorous acid derivatives being diasteroisomers or enantiomers. Application as drugs.
Cette invention concerne des dérivés acides hypophosphorés représentés par la formule (I). Dans cette formule, M est un groupe [C(R3,R4)]n1 - C(E,COOR1, N(H, Z)), ou un groupe Ar-CH(COOR1, N(H, Z)) éventuellement substitué, ou un acide aminé a, ß, ou g-cyclique; . R1 est H ou R, R étant un groupe protecteur hydroxy ou carboxy; . Z est H ou un groupe amino protecteur R', benzyl oxycarbonyl, benzyle ou substitué benzyle; E est H ou un C1-C3 alkyle, aryle, un groupe hydrophobe; . R2 est pris dan le groupe comprenant: D-CH(R6)- C-(R7, R8), (R11,R12)CH- C(R9, R10), D - CH(OH), D- [C(R13, R14)]n3 -, C[(R15, R16, R17)]n4, D-CH2, (R18)CH = C(R19), D-(M1)n6-CO, PO(OH)2-CH2 ou (PO(OH)2-CH2), (COOH-CH2)-CH2, avec - D = H, OH, OR, (CH2)n2OH, (CH2)n1OR, COOH, COOR, (CH2)n2COOH, (CH2)n1COOR, SR, S(OR), SO2R, NO2, hétéroaryle, C1-C3 alkyle, cycloalkyle, hétérocycloalkyle, (CH2)n2-alkyle, (COOH, NH2)-(CH2)u1-cyclopropyl-(CH2)u2-, CO-NH-alkyle, Ar, (CH2)n2-Ar, CO-NH-Ar; - R3 à R19 étant H, OH, OR, (CH2)n2OH, (CH2)n1OR, COOH, COOR, (CH2)n2COOH, (CH2)n1COOR, C1-C3 alkyle, cycloalkyle, (CH2)n1-alkyle, aryle, (CH2)n1-aryle, halogène, CF3, SO3H, (CH2)x PO3H2, avec x = 0, 1 ou 2, B(OH)2,, NO2, SO2NH2, SO2NHR; SR, S(O)R, SO2R, benzyle; - M1 est un groupe alkylène ou arylène; - n1= 1, 2 ou 3, n2= 1, 2 ou 3, n3= 0, 1, 2 ou 3 et n4= 1, 2 ou 3, n5= 1,2 ou 3, n6= 0 or 1, u1 and u2, identiques ou différents = 0,1 ou 2, à condition quela formule (I) ne représenter pas la forme racémique (3R, S) ni la forme énantiomère (3R) de 3 amino,3-carboxy-propyl-2'-carboxy-éthylphosphinique acide; 3 amino,3-carboxy-propyl- 4'carboxy,2'carboxy-butanoylphosphinique acide; 3 amino,3-carboxy-propyl- 2'carboxy-butanoylphosphinique acide; 3 amino,3-carboxy-propyl- 3'amino, 3'carboxy-propylylphosphinique acide; and 3 amino,3-carboxypropyl -7'amino-2', 7'-dicarboxyheptylphosphinique acide, lesdits dérivées acides hypophosphorés étant des diastero-isoméres ou des énantiomères. Cette invention concerne également l'application de ces dérivés en tant que médicaments.
Acher Francine
Bertrand Hugues-Olivier
Pin Jean-Philippe
Selvam Chelliah
Triballeau Nicolas
Bereskin & Parr Llp/s.e.n.c.r.l.,s.r.l.
Centre National de La Recherche Scientifique (cnrs)
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