Pharmaceutical compositions comprising anti-inflammatory quinazolinecarboxamide derivatives
AssigneeRimonyx Pharmaceuticals Ltd.
InventorsPaul Gregor, Nicholas Harris, Juraj Koppel, Regina Zhuk
Life of this patent
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Abstract
The present invention provides pharmaceutical compositions comprising quinazolinecarboxamide derivative, and certain novel quinazolinecarboxamide derivatives capable of inhibiting heparan sulfate-glycosaminoglycan (HS-GAGs) interactions with L-selectin, and useful in the prevention or treatment of various diseases, disorders and conditions mediated by HS-GAGs, particularly inflammatory and autoimmune diseases, viral diseases, cancer, and amyloid disorders.
Claims35
A pharmaceutical composition comprising a pharmaceutically acceptable diluent or carrier and an active ingredient of the general formula I:
- wherein:
- R1 is optionally substituted hydrocarbyl or heterocyclyl;
- R2 is selected from the group consisting of H, (C1-C12)alkyl, (C6-C14)aryl-CH2-, heteroaryl-CH2-, alkylcarbonyl-CH2-, (C6-C14) arylcarbonyl-CH2- and heteroarylcarbonyl-CH2-;
- R3 and R4 each is selected from the group consisting of hydrogen, C1-C6 alkyl, (C1-C6)alkoxy(C1-C6)alkyl, and C1-C6 alkyl substituted by a group containing a basic nitrogen atom or by a 5-7 membered heterocyclic ring containing one or two heteroatoms, one of them being a basic nitrogen atom, or R3 and R4 together with the nitrogen atom to which they are attached form a 5-7 membered saturated heterocyclic ring containing one or two basic nitrogen atoms, optionally substituted on the additional nitrogen atom;
- and pharmaceutically acceptable salts thereof.
2-17. (canceled)
23-28. (canceled)
33-42. (canceled)
The compound 2-[[(6-nitro-4H-1,3-benzodioxin -8-yl)methyl]thio]-3-(2-propenyl)-3,4-dihydro-4-oxo -N-[3-(4-morpholinyl)propyl]-7-quinazoline carboxamide (Compound No. 2010).
The compound 2-[[(5-acetyl-2-methoxyphenyl) methyl)thio]-3-(phenyl-methyl)-3,4-dihydro-4-oxo -N-[3-(1H-imidazol-1-yl)propyl]-7-quinazoline-carboxamide (Compound No. 2011).
The compound 2-[[(5-acetyl-2-methoxyphenyl) methyl]thio]-3-(phenyl-methyl)-3,4-dihydro-4-oxo -N-(1-ethyl-piperidin-4-yl)-7-quinazolinecarboxamide (Compound No. 2012).
A method for the treatment or prevention of diseases, disorders or conditions related to cell adhesion or cell migration mediated by heparan sulfate glycosaminoglycans, comprising the step of administering to a subject in need thereof a therapeutically effective amount of a pharmaceutical composition comprising a compound of the general formula I:
- wherein:
- R1 is optionally substituted hydrocarbyl or heterocyclyl;
- R2 is selected from the group consisting of H, (C1-C12)alkyl, (C6-C14)aryl-CH2-, heteroaryl-CH2-, alkylcarbonyl-CH2-, (C6-C 14)arylcarbonyl-CH2-, and heteroarylcarbonyl-CH2-;
- R3 and R4 each is selected from the group consisting of hydrogen, C1-C6 alkyl, (C1-C6)alkoxy(C1-C6)alkyl, and C1-C6 alkyl substituted by a group containing a basic nitrogen atom or by a 5-7 membered heterocyclic ring containing one or two heteroatoms, one of them being a basic nitrogen atom, or R3 and R4 together with the nitrogen atom to which they are attached form a 5-7 membered saturated heterocyclic ring containing one or two basic nitrogen atoms, optionally substituted on the additional nitrogen atom;
- and pharmaceutically acceptable salts thereof.
47-62. (canceled)
67-72. (canceled)
Dependencies are inferred from the claim text.