C - Chemistry – Metallurgy – 07 – F
Patent
C - Chemistry, Metallurgy
07
F
C07F 9/30 (2006.01) A61K 31/662 (2006.01) A61P 25/00 (2006.01)
Patent
CA 2694462
The invention relates to thiophosphi(o)nic 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 (Ar designating an aryl or an heteroaryl group), or an .alpha., .beta. cyclic aminoacid group such as, formula (II) or a .beta., .gamma.-cyclic aminoacid group such as, formula (III). R1 is H or R, R being an hydroxy or a carboxy protecting group, such as C1-C3 alkyl, Ar (being aryl or heteroaryl),. Z is H or an amino protecting group R', such as C1-C3 alkyl, C1-C3 acyl, Boc, Fmoc, COOR, benzyl oxycarbonyl, benzyl or benzyl substituted such as defined with respect to Ar;. E is H or a C1-C3 alkyl, aryl, an hydrophobic group such as (CH2)n1 -alkyl, (CH2)n1-aryl (or heteroaryl), such as a benzyl group, or a xanthyl, alkyl xanthyl or alkyl thioxanthyl group, or -(CH2)n1-cycloalkyl, -(CH2)n-(CH2-Ar)2, a chromanyl group, particularly 4-methyl chromanyle, indanyle, tetrahydro naphtyl, particularly methyl-tetrahydronaphtyl; or M is OM', wherein M' is as above defined for M;. 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- D-C(R,R')-O- D-O-, formula (IV), 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)n1C00R, 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, R being as above defined and Ar being an optionally substituted aryl or heteroaryl group, - R3 to R19, identical or different, 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 (V), NO2, SO2NH2, SO2NHR; SR, S(O)R, SO2R, benzyl; one of R11 or R12 being COOR, COOH, (CH2)n2- COOH, (CH2)n2-COOR, PO3H2 the other one being such as defined for R9 and R10; - one Of R15, R16 and R17 is COOH or COOR, the others, identical or different, being such as above defined; - one of R18 and R19 is COOH or COOR, the other being such as
L'invention concerne des dérivés de l'acide thiophosphi(o)nique de formule (I) dans laquelle M est un groupe [C(R3,R4)]n1 - C(E,COOR1, N(H, Z)), ou un groupe Ar-CH(COOR1, N(H, Z)) facultativement substitué (Ar représentant un groupe aryle ou hétéroaryle), ou un groupe acide a, ß-aminé cyclique tel que, ou un groupe acide ß, ?- aminé cyclique tel que. R1 est H ou R, R étant un groupe protégeant le groupe hydroxy ou carboxy, tel qu'un groupe alkyle en C1-C3, Ar (Ar représentant un groupe aryle ou hétéroaryle),. Z est H ou un groupe protégeant l'amine R', tel qu'un groupe alkyle en C1-C3, acyle en C1-C3, Boc, Fmoc, COOR, benzyloxycarbonyle, benzyle ou benzyle substitué tel que défini par rapport à Ar;. E est H ou un groupe alkyle en C1-C3, aryle, un groupe hydrophobe tel que (CH2)n1-alkyle, (CH2)n1-aryle (ou hétéroaryle), tel qu'un groupe benzyle, ou un groupe xanthyle, alkylxanthyle ou alkylthioxanthyle, ou -(CH2)n1-cycloalkyle, -(CH2)n-(CH2-Ar)2, un groupe chromanyle, en particulier 4-méthylchromanyle, indanyle, tétrahydronaphtyle, en particulier méthyl-tétrahydronaphtyle; ou M est OM', où M' est tel que défini ci-dessus pour M;. R2 est choisi dans le groupe constitué par 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- D-C(R,R')-O- D-O- 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, alkyle en C1-C3, cycloalkyle, hétérocycloalkyle, (CH2)n2-alkyle, (COOH, NH2)-(CH2)u1-cyclopropyl-(CH2)u2-, CO-NH-alkyle, Ar, (CH2)n2-Ar, CO-NH-Ar, R étant tel que défini ci-dessus et Ar étant un groupe aryle ou hétéroaryle facultativement substitué, - R3 à R19, identiques ou différents, étant H, OH, OR, (CH2)n2OH, (CH2)n1OR, COOH, COOR, (CH2)n2COOH, (CH2)n1COOR, alkyle en C1-C3, cycloalkyle, (CH2)n1-alkyle, aryle, (CH2)n1-aryle, N-N halogène, CF3, SO3H, (CH2)X PO3H2, avec x = 0, 1 ou 2, B(OH)2, NO2, SO2NH2, SO2NHR; SR, S(O)R, SO2R, benzyle; un de R11 ou R12 étant COOR, COOH, (CH2)n2-COOH, (CH2)n2-COOR, PO3H2, l'autre étant tel que défini pour R9 et R10; - un de R15, R16 et R17 est COOH ou COOR, les autres, identiques ou d
Acher Francine
Pin Jean-Philippe
Selvam Chelliah
Benoit & Cote Associes Inc.
Centre National de La Recherche Scientifique (cnrs)
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