Quinazolinone derivatives as cholecystokinin (CCK) ligands
First Claim
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1. A process of preparing a 2-amino compound of the structure:
- ##STR36## wherein W, X, Y, and Z are each independently selected from C--R3, C--R4, C--R5, C--R6 and N (nitrogen) and that no more than two of W, X, Y and Z are N;
wherein R3, R4, R5 and R6 are each independently hydrogen, hydroxy, sulfhydryl, lower alkoxy (1-4 carbon atoms), lower thioalkoxy (1-4 carbon atoms), lower alkyl (1-4 carbon atoms), halo, CN, CF3, NO2, COOR7 or NR7 R8 ;
wherein R7 and R8 are independently hydrogen or lower alkyl (1-4 carbon atoms);
R2 is;
an alkyl of 1 to 6 carbon atoms,unsubstituted, mono- or polysubstituted phenyl or polyaromatic,unsubstituted, mono- or polysubstituted heteroaromatic with hetero atom(s) N (nitrogen), O (oxygen) and/or S (sulfur), orunsubstituted, mono- or polysubstituted aralkyl,unsubstituted, mono- or polysubstituted cyclo or polycycloalkyl hydrocarbon, ormono- or polyheterocycle (3-8 atoms per ring) with 1 to 4 hetero atoms as N (nitrogen), O (oxygen), or S (sulfur);
wherein substitutions are selected from hydrogen, methyl, methoxy, fluorine, chlorine, bromine, iodine, hydroxy, ethoxy, propoxy, i-propoxy, t-butoxy, ethyl, propyl, i-propyl, trifluoromethyl, 3-cyclopropoxy, thioisopropyl, cyano, N,N-dimethylamino, N,N-dimethylamino methyl, carboxy, carbmethoxy, and tetrazole;
comprising the steps of;
(a) reacting the 2-hydrazine precursor with hydrogen;
in presence of a catalyst optionally Raney nickel, and(b) recovering the 2-amino product.
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Abstract
Novel quinazolinone derivatives with good binding affinity for the CCK-A and CCK-B receptors, pharmaceutical compositions containing them, methods of using them and a novel process for their preparation are taught. The compounds are useful agents to suppress appetite, reduce gastric acid secretion, and the like.
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Citations
9 Claims
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1. A process of preparing a 2-amino compound of the structure:
- ##STR36## wherein W, X, Y, and Z are each independently selected from C--R3, C--R4, C--R5, C--R6 and N (nitrogen) and that no more than two of W, X, Y and Z are N;
wherein R3, R4, R5 and R6 are each independently hydrogen, hydroxy, sulfhydryl, lower alkoxy (1-4 carbon atoms), lower thioalkoxy (1-4 carbon atoms), lower alkyl (1-4 carbon atoms), halo, CN, CF3, NO2, COOR7 or NR7 R8 ; wherein R7 and R8 are independently hydrogen or lower alkyl (1-4 carbon atoms); R2 is; an alkyl of 1 to 6 carbon atoms, unsubstituted, mono- or polysubstituted phenyl or polyaromatic, unsubstituted, mono- or polysubstituted heteroaromatic with hetero atom(s) N (nitrogen), O (oxygen) and/or S (sulfur), or unsubstituted, mono- or polysubstituted aralkyl, unsubstituted, mono- or polysubstituted cyclo or polycycloalkyl hydrocarbon, or mono- or polyheterocycle (3-8 atoms per ring) with 1 to 4 hetero atoms as N (nitrogen), O (oxygen), or S (sulfur); wherein substitutions are selected from hydrogen, methyl, methoxy, fluorine, chlorine, bromine, iodine, hydroxy, ethoxy, propoxy, i-propoxy, t-butoxy, ethyl, propyl, i-propyl, trifluoromethyl, 3-cyclopropoxy, thioisopropyl, cyano, N,N-dimethylamino, N,N-dimethylamino methyl, carboxy, carbmethoxy, and tetrazole; comprising the steps of; (a) reacting the 2-hydrazine precursor with hydrogen;
in presence of a catalyst optionally Raney nickel, and(b) recovering the 2-amino product. - View Dependent Claims (2, 3, 4, 8)
- ##STR36## wherein W, X, Y, and Z are each independently selected from C--R3, C--R4, C--R5, C--R6 and N (nitrogen) and that no more than two of W, X, Y and Z are N;
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5. A process of preparing the 2-amino product of the structure:
- ##STR37## wherein W, X, Y and Z are each independently selected from C--R3, C--R4, C--R5, C--R6 and N (nitrogen) and that no more than two of W, X, Y, and Z are N;
wherein R3, R4, R5 and R6 are each independently hydrogen, hydroxy, sulfhydryl, lower alkoxy (1-4 carbon atoms), lower thioalkoxy (1-4 carbon atoms), lower alkyl (1-4 carbon atoms), halo, CN, CF3, NO2, COOR7 or NR7 R8 ; wherein R7 and R8 are independently hydrogen or lower alkyl (1-4 carbon atoms); M is oxygen; R2 is; an alkyl of 1 to 6 carbon atoms, unsubstituted, mono- or polysubstituted phenyl or polyaromatic, unsubstituted, mono- or polysubstituted heteroaromatic with hetero atom(s) N (nitrogen), O (oxygen), and/or S (sulfur) or, unsubstituted, mono- or polysubstituted aralkyl, unsubstituted, mono- or polysubstituted cyclo or polycycloalkyl hydrocarbon, or mono- or polyheterocycle (3-8 atoms per ring) with 1 to 4 hetero atoms as N (nitrogen), O (oxygen), or S (sulfur); and wherein substitutions are selected from hydrogen, methyl, methoxy, fluorine, chlorine, bromine, iodine, hydroxy, ethoxy, propoxy, i-propoxy, t-butoxy, ethyl, propyl, i-propyl, trifluoromethyl, 3-cyclopropoxy, thioisopropyl, cyano, N,N-dimethylamino, N,N-dimethylamino methyl, carboxy, carbmethoxy, and tetrazole; comprising the steps of; (a) reacting hydrazine with a compound of the structure;
##STR38## (b) hydrogenating the product of step (a); and
(c) recovering the 2-amino product. - View Dependent Claims (6)
- ##STR37## wherein W, X, Y and Z are each independently selected from C--R3, C--R4, C--R5, C--R6 and N (nitrogen) and that no more than two of W, X, Y, and Z are N;
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7. A method of producing the compound of Formula I ##STR40## comprising reacting R2 NH2 with a compound of Formula II:
- ##STR41## wherein B is defined as a direct bond or, ##STR42## wherein i and j are independently 0 or 1;
R9 and R10 are independently hydrogen, lower alkyl (1-4 carbon atoms), or lower alkoxy (1-4 carbon atoms);A is selected from the group consisting of;
##STR43## wherein W, X, Y and Z are each independently selected from C--R3, C--R4, C--R5, and N (nitrogen) and that no more than two of W, X, Y, and Z are N;wherein R3, R4, R5 and R6 are each independently hydrogen, hydroxy, sulfhydryl, lower alkoxy (1-4 carbon atoms), lower thioalkoxy (1-4 carbon atoms), lower alkyl (1-4 carbon atoms), halo, CN, CF3, NO2, COOR7 or NR7 R8 ; wherein R7 and R8 are independently hydrogen or lower alkyl (1-4 carbon atoms); M is oxygen or sulfur; wherein R11 and R12 are independently hydrogen or lower alkyl (1-4 carbon atoms);
n=0 or 1;R1 is; an alkyl of 1 to 6 carbon atoms, unsubstituted, mono- or polysubstituted phenyl or polyaromatic, unsubstituted, mono- or polysubstituted heteroaromatic with hetero atom(s) N (nitrogen), O (oxygen), and/or S (sulfur), unsubstituted, mono- or polysubstituted aralkyl, unsubstituted, mono- or polysubstituted cyclo or polycycloalkyl hydrocarbon, or mono- or polyheterocycle (3 to 8 atoms per ring) with 1 to 4 hetero atoms selected from the group consisting of N (nitrogen), O (oxygen), and S (sulfur); wherein the substitutions are selected from hydrogen, methyl, methoxy, fluorine, bromine, chlorine, iodine, trifluoromethyl, cyano, acetyl, carboxy, carbmethoxy, carbethoxy, amino, N,N-dimethylamino, amido, acetyl, methylene carboxy, tetrazole, nitro, cyclohexyl, and adamantyl; R2 is; an alkyl of 1 to 6 carbon atoms, unsubstituted, mono- or polysubstituted phenyl or polyaromatic, unsubstituted, mono- or polysubstituted heteroaromatic with hetero atom(s) N (nitrogen), O (oxygen), and/or S (sulfur), or unsubstituted, mono- or polysubstituted cyclo or polycycloalkyl hydrocarbon, or mono- or polyheterocycle (3-8 atoms per ring) with 1 to 4 hetero atoms selected from the group consisting of N (nitrogen), O (oxygen), and S (sulfur); and wherein substitutions are selected from hydrogen, methyl, methoxy, fluorine, chlorine bromine, iodine, hydroxy, ethoxy, propoxy, i-propoxy, t-butoxy, ethyl, propyl, i-propyl, trifluoromethyl, 3-cyclopropoxy, thioisopropyl, cyano, N,N-dimethylamino, N,N-dimethylamino methyl, carboxy, carbmethoxy, and tetrazole. - View Dependent Claims (9)
- ##STR41## wherein B is defined as a direct bond or, ##STR42## wherein i and j are independently 0 or 1;
Specification
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Current AssigneeWarner-Lambert Company (Pfizer Inc.)
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Original AssigneeWarner-Lambert Company (Pfizer Inc.)
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InventorsPadia, Janak Khimchand
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Primary Examiner(s)Grumbling, Matthew V.
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Application NumberUS08/826,843Time in Patent Office672 DaysField of Search544/236, 544/256, 544/257, 544/258, 544/259, 544/260, 544/280, 544/284, 544/287US Class Current544/236CPC Class CodesC07D 239/50 Three nitrogen atomsC07D 239/91 with aryl or aralkyl radica...C07D 239/95 with hetero atoms directly ...C07D 403/12 linked by a chain containin...
