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US 7,405,231 B2Granted
Oxidized thioether derivatives
AssigneeHoffmann-La Roche Inc.
InventorsBirgit Bossenmaier, Walter-Gunar Friebe, Thomas Friess, Lothar Kling, Matthias Rueth, Edgar Voss
Life of this patent
Estimating the term…
Abstract
The present invention provides the compounds of formula I their pharmaceutically acceptable salts or esters, enantiomeric forms, diastereoisomers and racemates, the preparation of the above-mentioned compounds, pharmaceutical compositions containing them and their manufacture, as well as the use of the above-mentioned compounds in the control or prevention of illnesses such as cancer.
Claims18
A compound of formula I
- wherein:
- R1 is selected from the group consisting of:
- (a) —S(O)CH3,
- (b) —S(O)CF3,
- (c) S(O)2CH3, and
- (d) S(O)2CF3;
- R2 is selected from the group consisting of:
- (a) hydrogen,
- (b) fluorine, and
- (c) chlorine;
- R3 is selected from the group consisting of:
- (a) hydrogen,
- (b) (C1-C3)alkyl,
- (c) (C1-C3)alkoxy, and
- (d) halogen;
- G is selected from the group consisting of:
- (a) —NH—,
- (b) —S—, and
- (c) —O—;
- V is selected from the group consisting of:
- (a) —O—, and
- (b) —S(O)x—;
- W is selected from the group consisting of:
- (a) —CH2—;
- and
- (b) a direct bond;
- X is selected from the group consisting of:
- (a) —NH—,
- (b) —O—,
- (c) —S(O)x—,
- (d) —C(O)—,
- (e) —C(O)NH—,
- (f) —NHC(O)—,
- (g) —S(O)2NH—,
- (h) —NHS(O)2—,
- (i) —CH═CH—,
- (j) —C≡C—, and
- (k) —CH2—;
- Y is —(CH2)n-;
- B is selected from the group consisting of:
- (a) imidazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- (b) pyrazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- (c) triazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- and
- (d) tetrazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- n is 1, 2 or 3;
- and
- x is 0, 1 or 2;
- or a pharmaceutically acceptable salt or ester thereof.
98 more elements
A pharmaceutical composition comprising, (i) a therapeutically effective amount of a compound of formula I or a pharmaceutically acceptable salt or ester thereof, and (ii) a pharmaceutically acceptable carrier;
- wherein formula I is:
- wherein:
- R1 is selected from the group consisting of:
- (a) —S(O)CH3,
- (b) —S(O)CF3,
- (c) S(O)2CH3, and
- (d) S(O)2CF3;
- R2 is selected from the group consisting of:
- (a) hydrogen,
- (b) fluorine, and
- (c) chlorine;
- R3 is selected from the group consisting of:
- (a) hydrogen,
- (b) (C1-C3)alkyl,
- (c) (C1-C3)alkoxy, and
- (d) halogen;
- G is selected from the group consisting of:
- (a) —NH—,
- (b) —S—, and
- (c) —O—;
- V is selected from the group consisting of:
- (a) —O—, and
- (b) —S(O)x—;
- W is selected from the group consisting of:
- (a) —CH2—;
- and
- (b) a direct bond;
- X is selected from the group consisting of:
- (a) —NH—,
- (b) —O—,
- (c) —S(O)x—,
- (d) —C(O)—,
- (e) —C(O)NH—,
- (f) —NHC(O)—,
- (g) —S(O)2NH—,
- (h) —NHS(O)2—,
- (i) —CH═CH—,
- (j) —C≡C—, and
- (k) —CH2—;
- Y is —(CH2)n-;
- B is selected from the group consisting of:
- (a) imidazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)hd x-, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- (b) pyrazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- (c) triazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- and
- (d) tetrazolyl, which is:
- (1) unsubstituted;
- or
- (2) once substituted with —C(O)OH;
- or
- (3) one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- or
- (4) once substituted with —C(O)OH and one, two or three times substituted with alkyl, which alkyl is:
- (A) optionally interrupted one, two, or three times by —O—, —S(O)x—, —S(O)2NH—, —NHS(O)2—, —C(O)—NH—, —NH—C(O)—, or —P(O)(CH3)—;
- and
- (B) unsubstituted or one, two or three times substituted with —OH, —NH2, —C(O)OH, or —P(O)(CH3)2;
- n is 1, 2 or 3;
- and
- x is 0, 1 or 2.
98 more elements
Dependencies are inferred from the claim text.