US 2006/0235013 A1Published application

Tricyclic azole derivatives

OwnerGuy Georges, Bernhard Goller +5inventors

InventorsGuy Georges, Bernhard Goller, Hans-Willi Krell, 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.

Claims20

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—R4;
(3) alkenyl, which is optionally substituted one or more times with nitro, cyano or —Y—R4;
and
(4) alkynyl, which is optionally substituted one or more times with nitro, cyano or —Y—R4;
(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) R4 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 morel 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) X is a single bond, —CH2— or —C(alkyl)2—;
(f) ring A is a 5 to 7 membered saturated ring optionally substituted one or more times by alkyl and optionally containing one or two heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur, with the remaining ring atoms being carbon atoms, wherein if said ring A contains one nitrogen, said nitrogen can be optionally substituted once by a substituent selected from the group consisting of:
(1) —CH2-phenyl;
(2) —C(O)-alkyl;
(3) —C(O)-cycloalkyl;
(4) —C(O)-heterocyclyl;
(5) —C(O)—(CH2)n-phenyl, wherein the phenyl is optionally substituted once or twice with halogen, alkyl, alkoxy, nitro, amino, alkylamino, dialkylamino, cyano, trifluoromethyl or trifluoromethoxy;
(6) —C(O)—(CH2)n-heteroaryl;
(7) —C(O)—NH-phenyl, wherein the phenyl is optionally substituted once or twice with halogen, alkyl, alkoxy, nitro, amino, alkylamino, dialkylamino, cyano, trifluoromethyl or trifluoromethoxy;
and
(8) —S(O)2-phenyl, wherein the phenyl is optionally substituted once or twice with halogen, alkyl, alkoxy, nitro, amino, alkylamino, dialkylamino, cyano;
trifluoromethyl or trifluoromethoxy;
and
(g) n is 0, 1 or 2.

51 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—R4;
(3) alkenyl, which is optionally substituted one or more times with nitro, cyano or —Y—R4;
and
(4) alkynyl, which is optionally substituted one or more times with nitro, cyano or —Y—R4;
(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) R4 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 morel 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) X is a single bond, —CH2— or —C(alkyl)2—;
(f) ring A is a 5 to 7 membered saturated ring optionally substituted one or more times by alkyl and optionally containing one or two heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur, with the remaining ring atoms being carbon atoms, wherein if said ring A contains one nitrogen, said nitrogen can be optionally substituted once by a substituent selected from the group consisting of:
(1) —CH2-phenyl;
(2) —C(O)-alkyl;
(3) —C(O)-cycloalkyl;
(4) —C(O)-heterocyclyl;
(5) —C(O)—(CH2)n-phenyl, wherein the phenyl is optionally substituted once or twice with halogen, alkyl, alkoxy, nitro, amino, alkylamino, dialkylamino, cyano, trifluoromethyl or trifluoromethoxy;
(6) —C(O)—(CH2)n-heteroaryl;
(7) —C(O)—NH-phenyl, wherein the phenyl is optionally substituted once or twice with halogen, alkyl, alkoxy, nitro, amino, alkylamino, dialkylamino, cyano, trifluoromethyl or trifluoromethoxy;
and
(8) —S(O)2-phenyl, wherein the phenyl is optionally substituted once or twice with halogen, alkyl, alkoxy, nitro, amino, alkylamino, dialkylamino, cyano;
trifluoromethyl or trifluoromethoxy;
and
(g) n is 0, 1 or 2.

51 more elements