US 2006/0235065 A1Published application

Aminopyrazole derivatives

AssigneeHoffmann-La Roche Inc.

InventorsGuy Georges, Bernhard Goller, Klaus-Peter Kuenkele, Aude Lemarchand, Anja Limberg, Ulrike Reiff, Petra Rueger, Matthias Rueth

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Abstract

The present invention relates to 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 such compounds in the control or prevention of illnesses such as cancer.

Claims40

Dependent claims

A compound according to formula I and all pharmaceutically acceptable salts or esters thereof wherein formula I is:

wherein:
(a) R1 is selected from the group consisting of:
(1) hydrogen;
(2) alkyl, which is optionally substituted one or more times with nitro, cyano or —Y—R6;
(3) alkenyl, which is optionally substituted one or more times with nitro, cyano or —Y—R6;
and
(4) alkynyl, which is optionally substituted one or more times with nitro, cyano or —Y—R6;
(b) Y is selected from the group consisting of:
(1) a single bond;
(2) —C(O)NH—;
(3) —C(O)N(alkyl)-;
(4) —N(alkyl)C(O)—;
(5) —NHC(O)—;
(6) —NHC(O)NH—;
(7) —NHC(O)N(alkyl)-;
(8) —NHS(O)2—;
(9) —S(O)2NH—;
(10) —S(O)2N(alkyl)-;
(11) —S(O)2—;
(12) —S(O)—;
(13) —C(O)O—;
(14) —OC(O)—;
(15) —C(O)—;
(16) —P(O)(alkyl)-;
(17) —NH—;
(18) —N(alkyl)-;
(19) —O—;
and
(20) —S—;
(c) R6 is selected from the group consisting of:
(1) alkyl, which is optionally substituted one or more times by halogen, hydroxy, alkoxy, alkoxyalkoxy, amino, alkylamino, dialkylamino, —C(O)OH or —C(O)NH2;
(2) aryl, which is optionally substituted one or more times by halogen, cyano, nitro, amino, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy, halogenated (C1-C4)alkyl or halogenated (C1-C4)alkoxy;
(3) heteroaryl, which is optionally substituted one or more times by alkyl;
(4) cycloalkyl;
and
(5) heterocyclyl;
(d) R2 and R3 form together with the carbon atom to which they are attached a (C5-C6)cycloalkyl ring, or alternatively, R2 and R3 are independently selected from the group consisting of:
(1) hydrogen;
and
(2) alkyl;
(e) Z is selected from the group consisting of:
(1) —C(O)—,
(2) —C(O)NR7,
(3) —C(O)O—,
(4) —S(O)2—, and
(5) —S(O)2NR7—;
(f) n is 0 or 1;
(g) R7 is hydrogen or alkyl;
(h) R4 is selected from the group consisting of:
(1) hydrogen;
(2) alkyl, which is optionally substituted one or more times by halogen, hydroxy, alkoxy, alkoxyalkoxy, amino, alkylamino or dialkylamino;
(3) aryl-V—, wherein the aryl is optionally substituted one or more times by halogen, cyano, nitro, amino, alkylamino, dialkylamino, 2,4-dioxa-pentan-1,5-diyl, 2,5-dioxa-hexan-1,6-diyl, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy, halogenated (C1-C4)alkyl or halogenated (C1-C4)alkoxy;
(4) heteroaryl-V—, wherein the heteroaryl is optionally substituted one or more times by alkyl;
(5) cycloalkyl-V—;
and
(6) heterocyclyl-V—;
with the proviso that R4 is not hydrogen, if n is 1 and Z is —C(O)O—;
(i) V is selected from the group consisting of:
(1) a single bond,
(2) alkylene,
(3) —O-alkylene,
(4) cycloalkylene, and
(5) alkenylene;
(j) R5 is selected from the group consisting of:
(1) hydrogen,
(2) alkyl,
(3) fluorine, and
(4) chlorine;
and
(k) X is a single bond, —CH2— or —C(alkyl)2—.

67 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound according to formula I and all pharmaceutically acceptable salts or esters thereof wherein formula I is:

wherein:
(a) R1 is selected from the group consisting of:
(1) hydrogen;
(2) alkyl, which is optionally substituted one or more times with nitro, cyano or —Y—R6;
(3) alkenyl, which is optionally substituted one or more times with nitro, cyano or —Y—R6;
and
(4) alkynyl, which is optionally substituted one or more times with nitro, cyano or —Y—R6;
(b) Y is selected from the group consisting of:
(1) a single bond;
(2) —C(O)NH—;
(3) —C(O)N(alkyl)-;
(4) —N(alkyl)C(O)—;
(5) —NHC(O)—;
(6) —NHC(O)NH—;
(7) —NHC(O)N(alkyl)-;
(8) —NHS(O)2—;
(9) —S(O)2NH—;
(10) —S(O)2N(alkyl)-;
(11) —S(O)2—;
(12) —S(O)—;
(13) —C(O)O—;
(14) —OC(O)—;
(15) —C(O)—;
(16) —P(O)(alkyl)-;
(17) —NH—;
(18) —N(alkyl)-;
(19) —O—;
and
(20) —S—;
(c) R6 is selected from the group consisting of:
(1) alkyl, which is optionally substituted one or more times by halogen, hydroxy, alkoxy, alkoxyalkoxy, amino, alkylamino, dialkylamino, —C(O)OH or —C(O)NH2;
(2) aryl, which is optionally substituted one or more times by halogen, cyano, nitro, amino, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy, halogenated (C1-C4)alkyl or halogenated (C1-C4)alkoxy;
(3) heteroaryl, which is optionally substituted one or more times by alkyl;
(4) cycloalkyl;
and
(5) heterocyclyl;
(d) R2 and R3 form together with the carbon atom to which they are attached a (C5-C6)cycloalkyl ring, or alternatively, R2 and R3 are independently selected from the group consisting of:
(1) hydrogen;
and
(2) alkyl;
(e) Z is selected from the group consisting of:
(1) —C(O)—,
(2) —C(O)NR7,
(3) —C(O)O—,
(4) —S(O)2—, and
(5) —S(O)2NR7—;
(f) n is 0 or 1;
(g) R7 is hydrogen or alkyl;
(h) R4 is selected from the group consisting of:
(1) hydrogen;
(2) alkyl, which is optionally substituted one or more times by halogen, hydroxy, alkoxy, alkoxyalkoxy, amino, alkylamino or dialkylamino;
(3) aryl-V—, wherein the aryl is optionally substituted one or more times by halogen, cyano, nitro, amino, alkylamino, dialkylamino, 2,4-dioxa-pentan-1,5-diyl, 2,5-dioxa-hexan-1,6-diyl, hydroxy, (C1-C4)alkyl, (C1-C4)alkoxy, halogenated (C1-C4)alkyl or halogenated (C1-C4)alkoxy;
(4) heteroaryl-V—, wherein the heteroaryl is optionally substituted one or more times by alkyl;
(5) cycloalkyl-V—;
and
(6) heterocyclyl-V—;
with the proviso that R4 is not hydrogen, if n is 1 and Z is —C(O)O—;
(i) V is selected from the group consisting of:
(1) a single bond,
(2) alkylene,
(3) —O-alkylene,
(4) cycloalkylene, and
(5) alkenylene;
(j) R5 is selected from the group consisting of:
(1) hydrogen,
(2) alkyl,
(3) fluorine, and
(4) chlorine;
and
(k) X is a single bond, —CH2— or —C(alkyl)2—.

67 more elements