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US 2004/0106667 A1Published application
Substituted indazoles, compositions containing them, method of production and use
AssigneeAventis Pharma S.A.
InventorsDominique Damour, Jean-Christophe Carry, Patrick Nemecek, Corinne Terrier, Frederico Nardi, Bruno Filoche, Marie-Pierre Cherrier, Daniel Bezard
Life of this patent
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Abstract
Substituted indazoles, compositions containing them, method of production and use. The present invention relates in particular to novel specific substituted indazoles exhibiting kinase-inhibiting activity, having therapeutic activity, in particlar in oncology.
Claims26
A product corresponding to the following formula (I):
- 255
- in which:
- h) [sic] R1 is selected from the group consisting of H, halogen, alkyl, alkylene [sic], alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted alkylene [sic], substituted alkynyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted heterocyclyl, CN, O(R2), OC(O)(R2), OC(O)N(R2)(R3), OS(O2)(R2), N(R2)(R3), N═C(R2)(R3), N(R2)C(O)(R3), N(R2)C(O)O(R3), N(R4)C(O)N(R2)(R3), N(R4)C(S)N(R2)(R3), N(R2)S(O2)(R3), C(O)(R2), C(O)O(R2), C(O)N(R2)(R3), C(═N(R3))(R2), C(═N(OR3))(R2), S(R2), S(O)(R2), S(O2)(R2), S(O2)N(R2)(R3), in which each R2, R3 and R4 is independently selected from the group consisting of H, alkyl, aryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted aryl, substituted cycloalkyl, substituted heterocyclyl, alkylene [sic], substituted alkylene [sic];
- i) [sic] X is selected from the group consisting of S(O2)—NH;
- S(O2)—O;
- NH—S(O2);
- O—S(O2);
- j) [sic] Z is selected from the group consisting of alkyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted heterocyclyl;
- with the proviso that the product of formula (I) is not one of the following compounds:
- 256
- in which alkyl is n-propyl, and in which Ra and Rb are independently selected from the group consisting of NH2, NO2 and Cl, or Ra and Rb form a ring —NH—CH═N—;
- 257
9 more elements
A product corresponding to the following formula (I):
- 258
- in which:
- k) [sic] R1 is selected from the group consisting of H, halogen, alkyl, alkylene [sic], alkynyl, aryl, heteroaryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted alkylene [sic], substituted alkynyl, substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted heterocyclyl, CN, O(R2), OC(O)(R2), OC(O)N(R2)(R3), OS(O2)(R2), N(R2)(R3), N═C(R2)(R3), N(R2)C(O)(R3), N(R2)C(O)O(R3), N(R4)C(O)N(R2)(R3), N(R4)C(S)N(R2)(R3), N(R2)S(O2)(R3), C(O)(R2), C(O)O(R2), C(O)N(R2)(R3), C(═N(R3))(R2), C(═N(OR3))(R2), S(R2), S(O)(R2), S(O2)(R2), S(O2)N(R2)(R3), in which each R2, R3 and R4 is independently selected from the group consisting of H, alkyl, aryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted aryl, substituted cycloalkyl, substituted heterocyclyl, alkylene [sic], substituted alkylene [sic];
- l) [sic] X is selected from the group consisting of S(O2)—NH;
- S(O2)—O;
- NH—S(O2);
- O—S(O2);
- m) [sic] Z is selected from the group consisting of alkyl, alkylene [sic], aryl, heteroaryl, cycloalkyl, heterocyclyl, substituted alkyl, substituted alkylene [sic], substituted aryl, substituted heteroaryl, substituted cycloalkyl, substituted heterocyclyl;
- n) [sic] R is chosen from H and C1-C3 alkyl
- with the proviso that the product of formula (I) is not one of the following compounds:
- 259
- 1°)
- in which
- (ix) [sic] Aryl is 3-fluorophenyl and Subst is chosen from methyl, 2,2,2-trifluoromethyl, 4-methylphenyl,
- 260
- (x) [sic] Aryl is chosen from 6-(2-dimethylaminomethyl-5-methylmorpholin-4-yl)-1H-benzimidazol-2-yl, 6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl, 6-(1,4′-bipiperidin-1′-yl)-1H-benzimidazol-2-yl and 6-(N,N-dialkylamino)-1H-benzimidazol-2-yl, and Subst is independently chosen from methyl, ethyl, trifluoromethyl, phenyl, 4-methoxyphenyl and thien-2-yl,
- (xi) [sic] Aryl is 4-fluorophenyl and Subst is phenyl,
- (xii) [sic] Aryl is 4-trifluoromethylphenyl and Subst is N,N-dimethylamino,
- (xiii) [sic] Aryl is thien-2-yl and Subst is 3,5-bis(trifluoromethyl)phenyl,
- (xiv) [sic] Aryl is 3,4-methylenedioxyphenyl and Subst is 1-methylethyl,
- (xv) [sic] Aryl is 3,5-bis(trifluoromethyl)phenyl and Subst is 5-(pyrid-2-yl)-thien-2-yl,
- (xvii) [sic] Aryl is 4-methoxyphenyl and Subst is 4-phenylsulfonylthien-2-yl,
- 261
- 2°)
- in which
- Subst is chosen from 3,4,5-trimethoxyphenyl, 2,3,4,5,6-pentafluorophenyl, methyl, and
- 262
- in which Ra and Rb are independently selected from the group consisting of NH2, NO2 and Cl, or Ra and Rb form a ring —NH—CH═N—.
25 more elements
The product as claimed in any one of the preceding claims, which is in the:
- 1) nonchiral form, or
- 2) racemic form, or
- 3) form enriched in a stereoisomer, or
- 4) form enriched in an enantiomer;
- and which is optionally salified.
2 more elements
A pharmaceutical composition comprising a product as claimed in any one of the preceding claims, in combination with a pharmaceutically acceptable excipient.
Dependencies are inferred from the claim text.