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US 2010/0166765 A1Published application
Benzoquinazoline derivatives
OwnerSandra Ammon, Rene Beerli +1inventors
InventorsSandra Ammon, Rene Beerli, Leo Widler
Life of this patent
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Abstract
A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof, wherein the groups R2, R3, R4, Q, X and Y are as defined in the specification, is useful in the treatment of bone conditions related to increased calcium depletion or resorption.
Claims16
A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof:
- wherein:
- Q is CH or N;
- R2 is C1-C4 alkyl;
- Y is selected from the group consisting of:
- R5-O—, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, R5-NH—;
- where R5 is C1-C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl;
- X is selected from the group consisting of aryl, heteroaryl, C1-C10 alkyl, C1-C10 alkyloxy, cycloalkyl, heterocycloalkyl, aryl C1-C4 alkyl, heteroaryl C1-C4 alkyl, cycloalkyl C1-C4 alkyl, heterocycloalkyl C1-C4 alkyl, arylamino, heteroarylamino, aryl C1-C4 alkylamino, heteroaryl C1-C4 alkylamino, C1-C6 alkylamino, C1-C6dialkylamino, aryloxy, heteroaryloxy, aryl C1-C4 alkyloxy, heteroaryl C1-C4 alkyloxy, cycloalkyl C1-C4 alkylamino, heterocycloalkyl C1-C4 alkylamino, cycloalkyl C1-C4 alkyloxy or heterocycloalkyl C1-C4 alkyloxy each of which is optionally substituted once or more;
- the optional substituent or substituents on X being independently selected from the group consisting of halo, cyano, trifluoromethyl, nitro, hydroxy, optionally substituted (C1-C4 alkyl, C1-C4 alkyloxy, amino, sulfanyl, sulfonyl, amino, oxycarbonyl, hydroxyl, sulfinyl, aminosulfonyl, sulfonylamino, carbonyl, carbonyloxy, carbonyl amino, carboxyl, acyl, acylamino, or carbamoyl);
- the optional substituent or substituents being selected from C1-C6 alkyl, C1-C6 alkyloxy, carboxyl, hydroxyl, hydroxy C1-C4 alkyl;
- each of which in turn may be optionally substituted by C1-C6 alkyloxy, C1-C6 alkyl, C1-C3 fluorinated alkyl, C1-C6 alkyloxy, carboxyl, hydroxyl, hydroxy C1-C4 alkyl, halo, cyano, nitro.
- R3 and R4 each represent one or more substituents independently selected from:
- H, halo, C1-C4 alkyl, C1-C4 alkyloxy, CF3;
- the optional substituent or substituents on R3 or R4 being independently selected from the group consisting of C1-C4 alkyl, halo, C1-C4 alkyloxy, cyano, sulfanyl, sulfonyl, amino, oxycarbonyl, hydroxyl which may in turn be optionally substituted once or more by C1-C4 alkyl, halo, C1-C4 alkyloxy, cyano, sulfanyl, sulfonyl, amino, oxycarbonyl or hydroxyl.
10 more elements
A compound of formula (I′) or a pharmaceutically acceptable salt or prodrug ester thereof:
- wherein:
- Q is CH or N;
- R2 is C1-C4 alkyl;
- Y is selected from the group consisting of:
- R5-O—, C1-C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, R5-NH—;
- where R5 is C1-C4 alkyl, C1-C4 alkenyl, C1-C4 alkynyl;
- X is selected from the group consisting of aryl, heteroaryl, C1-C6 alkyl, cycloalkyl, heterocycloalkyl, aryl C1-C4 alkyl, heteroaryl C1-C4 alkyl, arylamino, aryl C1-C4 alkylamino, heteroaryl C1-C4 alkylamino, C1-C6 alkylamino, C1-C6dialkylamino amino, aryloxy, heteroaryloxy, aryl C1-C4 alkyloxy, or heteroaryl C1-C4 alkyloxy, each of which is optionally substituted once or more;
- the optional substituent or substituents on X being independently selected from the group consisting of C1-C4 alkyl, halo, C1-C4 alkyloxy, cyano, trifluoromethyl, hydroxy, amino, nitro, alkyl, lower alkyl substituted (sulfanyl, sulfonyl, amino, oxycarbonyl, hydroxyl, sulfinyl, carbonyl, carboxyl, carbamoyl or aminoacyl);
- R3 and R4 each represent one or more substituents independently selected from:
- H, halo, optionally substituted C1-C4 alkyl, optionally substituted C1-C4 alkyloxy;
- the optional substituent or substituents on R3 or R4 being independently selected from the group consisting of C1-C4 alkyl, halo, C1-C4 alkyloxy, cyano, sulfanyl, sulfonyl, amino, oxycarbonyl, hydroxyl.
8 more elements
(canceled)
A process for preparation of a compound of formula (I) in free or salt form, comprising the step of:
- (i) for cases where Q is N, reacting a compound of formula (III) with a compound of formula (IV) and an ammonium salt in the presence of a suitable solvent:
- or
- (ii) reacting a compound of formula V
- wherein LG represents a suitable leaving group;
- with an organometallic reagent of formula VI:
- X-Met VI
- under suitable anhydrous conditions;
- or
- (iii) reacting a compound of formula Va
- with an organometallic reagent of formula VI:
- X-Met VI
- under suitable anhydrous conditions followed by oxidation to the carbonyl compound by an appropriate oxidation agent;
- or
- (iv) reacting a compound of formula VII
- with a compound X—H wherein the H forms part of an amino or hydroxy group, the reaction being carried out in the presence of a coupling reagent;
- or
- (v) reacting a compound of formula VIII
- wherein Hal is halogen or a leaving group
- with a compound X—H wherein the H forms part of an amino or hydroxy group, the reaction being carried out in the presence of a coupling reagent.
16 more elements
(canceled)
(canceled)
Dependencies are inferred from the claim text.