http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-063680-A1
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assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_42a59c5faed1d0699d86edc5a2eee671 |
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filingDate | 2007-08-03-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationDate | 2009-02-11-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
publicationNumber | AR-063680-A1 |
titleOfInvention | DERIVATIVES OF PIRAZOLO [1, 5-A] PYRIMIDINE, METHODS AND INTERMEDIARY FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS THAT INCLUDE THEM AND THEIR USE IN THE MANUFACTURE OF MEDICINES FOR THE TREATMENT OF DISEASES MEDITATED BY THE MODULATION OF MGLUR5. |
abstract | These compounds are potent modulators of mGluR5 and are useful, for example, for the treatment of various neurological disorders. Claim 1: A pyrazolo-pyrimidine compound of formula (1) wherein Y1, Y2 and Y3 independently are CR10, CR11, CR10R11, NR12, S or O, wherein at least one of Y1, Y2 and Y3 denotes CR10; or Y1 and Y2 together denote a group R10C = N; R10C = CR11; R10R11C-C (= O) or R12N- (C = O); or Y2 and Y3 together denote a group R10C = N; R10C = CR11; R10R11C-C (= O) or R12N- (C = O); R1 represents chlorine or bromine; R 2 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl or trifluoromethyl; R3 represents hydrogen, C1-6 alkyl, cycloaC3-7 alkyl or trifluoromethyl; or R2 and R3, together with the ring carbon atom, represent a carbonyl group; R4 represents hydrogen, C1-6 alkyl, C3-7 cycloalkyl or trifluoromethyl; R5 represents hydrogen, C1-6 alkyl, C3-7 cycloalkyl or trifluoromethyl; or R4 and R5, together with the carbon atom of the ring, represent a carbonyl group; R 6 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl or trifluoromethyl; R 7 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl or trifluoromethyl; R6 and R7, together with the ring carbon atom, represent a carbonyl group; R2 or R3, together with R6 or R7, can form a bivalent radical of the type CH2-CH2 or CH2-O; R10 and R11 independently represent hydrogen, halogen, amino, hydroxy, nitro, cyano, trifluoromethyl, trifluoromethoxy, aryl, C1-6 alkyl, C3-7 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C3 cycloalkyloxy -7, C2-6 alkenyloxy, C2-6 alkynyloxy, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy, heterocyclyloxy, C1-6 alkylamino, C1-6 di-alkylamino, C3-7 cycloalkylamino, C3-7 di-cycloalkylamino, C1- alkyl C3-7 6-cycloalkylamino, C2-6 alkylamino, C2-6 alkylamino, C2-6 di-alkylamino, C2-6 di-alkylamino, C1-6 alkyl-C2-6 alkylamino, C1-6 alkyl-C2-6 alkylamino , C2-6 alkenyl C3-7 cycloalkylamino, C2-6 alkynyl C3-7, C2-6 alkenyl C2-6 alkynyl, arylamino, diarylamino, aryl-C1-6 alkylamino, C2-6 aryl-alkylamino, aryl C2-6 -alkylamino, C3-7 aryl-cycloalkylamino, heteroarylamino, diheteroarylamino, heteroaryl-C 1-6 alkylamino, heteroaryl C2-6 alkylamino, heteroaryl-C2-6 alkylamino, heteroaryl-cycloalkylamino C3-7 not, heteroarilarilamino, heterocyclylamino, diheterocyclylamino, heterocyclylalkylamino C1-6, C2-6 heterocyclyl-alkenylamino, C2-6 alkynylamino heterocyclyl, heterocyclyl- C3-7 cycloalkylamino, heterociclilarilamino, heterociclilheteroarilamino, acyl, acyloxy, acylamino, alkoxycarbonyl C1- 6, C3-7 cycloalkoxycarbonyl, C2-6 alkenyloxycarbonyl, C2-6 alkynyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heterocyclyloxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di- alkylaminocarbonyl C1-6 cycloalkylaminocarbonylC7-carbonyl-C7-alkylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonyl , C1-6 alkylC3-7 cycloalkylaminocarbonyl, C2-6 alkenyl aminocarbonyl, C2-6 alkynyl aminocarbonyl, C2-6 di-alkylaminocarbonyl, C2-6 di-alkylaminocarbonyl, C1-6 alkyl-C2-6 alkylaminocarbonyl, C1-6-C2-6 alkynyl aminocarbonyl, C2-6 alkenyl C3-7 cycloalkylaminocarbonyl, C2-6 alkynyl C3-7 cycloalkylaminocarbonyl C2-6-C2-6 alkynylaminocarbonyl, arylaminocarbonyl, diarylaminocarbonyl, aryl-C 1-6 alkylaminocarbonyl, C 2-6 aryl-alkenylaminocarbonyl, C 2-6 aryl-alkylaminocarbonyl, C 3-7 aryl-cycloalkylaminocarbonyl, heteroarylaminocarbonyl, diheteroarylaminocarbonyl, heteroaryl-alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylarylcarbonyl-C 1-6 alkylarylcarbonyl-C 1-6 alkylaminocarbonyl-C 1 -C 6 -alkyl C2-6 alkynylaminocarbonyl, cycloalkylaminocarbonyl C3-7 heteroaryl-, heteroarilarilaminocarbonilo, heterocyclylaminocarbonyl, diheterocyclylamino-carbonyl, heterocyclyl-C1-6 alkylaminocarbonyl, heterocyclyl-C2-6 alkenylamino-carbonyl, heterocyclyl-C2-6 alkynylaminocarbonyl, heterocyclyl- C3-7 cycloalkylaminocarbonyl, heterociclilarilaminocarbonilo, heterociclilheteroarilamino-carbonyl, C1-6 alkylsulfinyl, C3-7 cycloalkylsulfinyl, C2-6 alkenylsulfinyl, C2-6 alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, heterocyclylsulfinyl, C1-6 alkylsulfonyl, C3-7 cycloalkylsulfonyl, C2-6 alkenylsulfonyl, alkynylsulfonyl C2- 6, arylsulfonyl, heteroarylsulfonyl, het erocyclylsulfonyl, C1-6 alkylsulfonylamino or arylsulfonylamino; and R 12 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, acyl, aryl, heteroaryl, heterocyclyl, C 1-6 alkylaminocarbonyl, C 1-6 alkylaminocarbonyl, alkylsulfonyl C1-6, arylsulfonyl or heteroarylsulfonyl; and pharmaceutically acceptable optical isomers, salts, hydrates, solvates and polymorphs of said compound. Claim 29: A process for the synthesis of a compound selected from those of formula (1) wherein: Y1, Y2 and Y3 independently are CR10, CR11, CR10R11, NR12, S or O, wherein at least one of Y1, Y2 and Y3 denotes CR10; or Y1 and Y2 together denote a group R10C = N; R10C = CR11; R10R11C-C (= O) or R12N- (C = O); or Y2 and Y3 together denote a group R10C = N; R10C = CR11; R10R11C-C (= O) or R12N- (C = O); R1 represents chlorine or bromine; R 2 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl or trifluoromethyl; R3 represents hydrogen, C1-6 alkyl, cycloaC3-7 alkyl or trifluoromethyl; or R2 and R3, together with the ring carbon atom, represent a carbonyl group; R4 represents hydrogen, C1-6 alkyl, C3-7 cycloalkyl or trifluoromethyl; R5 represents hydrogen, C1-6 alkyl, C3-7 cycloalkyl or trifluoromethyl; or R4 and R5, together with the carbon atom of the ring, represent a carbonyl group; R 6 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl or trifluoromethyl; R 7 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl or trifluoromethyl; R6 and R7, together with the ring carbon atom, represent a carbonyl group; R2 or R3, together with R6 or R7, can form a bivalent radical of the type CH2-CH2 or CH2-O; R10 and R11 independently represent hydrogen, halogen, amino, hydroxy, nitro, cyano, trifluoromethyl, trifluoromethoxy, aryl, C1-6 alkyl, C3-7 cycloalkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, C3 cycloalkyloxy -7, C2-6 alkenyloxy, C2-6 alkynyloxy, heteroaryl, heterocyclyl, aryloxy, heteroaryloxy, heterocyclyloxy, C1-6 alkylamino, C1-6 di-alkylamino, C3-7 cycloalkylamino, C3-7 di-cycloalkylamino, C1- alkyl C3-7 6-cycloalkylamino, C2-6 alkylamino, C2-6 alkylamino, C2-6 di-alkylamino, C2-6 di-alkylamino, C1-6 alkyl-C2-6 alkylamino, C1-6 alkyl-C2-6 alkylamino , C2-6 alkenyl C3-7 cycloalkylamino, C2-6 alkynyl C3-7, C2-6 alkenyl C2-6 alkynyl, arylamino, diarylamino, aryl-C1-6 alkylamino, C2-6 aryl-alkylamino, aryl C2-6 -alkylamino, C3-7 aryl-cycloalkylamino, heteroarylamino, diheteroarylamino, heteroaryl-C 1-6 alkylamino, heteroaryl C2-6 alkylamino, heteroaryl-C2-6 alkylamino, heteroaryl-cycloalkylamino C3-7 not, heteroarilarilamino, heterocyclylamino, diheterocyclylamino, heterocyclylalkylamino C1-6, C2-6 heterocyclyl-alkenylamino, C2-6 alkynylamino heterocyclyl, heterocyclyl- C3-7 cycloalkylamino, heterociclilarilamino, heterociclilheteroarilamino, acyl, acyloxy, acylamino, alkoxycarbonyl C1- 6, C3-7 cycloalkoxycarbonyl, C2-6 alkenyloxycarbonyl, C2-6 alkynyloxycarbonyl, aryloxycarbonyl, heteroaryloxycarbonyl, heterocyclyloxycarbonyl, aminocarbonyl, C1-6 alkylaminocarbonyl, di- alkylaminocarbonyl C1-6 cycloalkylaminocarbonylC7-carbonyl-C7-alkylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonylaminocarbonyl , C1-6 alkylC3-7 cycloalkylaminocarbonyl, C2-6 alkenyl aminocarbonyl, C2-6 alkynyl aminocarbonyl, C2-6 di-alkylaminocarbonyl, C2-6 di-alkylaminocarbonyl, C1-6 alkyl-C2-6 alkylaminocarbonyl, C1-6-C2-6 alkynyl aminocarbonyl, C2-6 alkenyl C3-7 cycloalkylaminocarbonyl, C2-6 alkynyl C3-7 cycloalkylaminocarbonyl C2-6-C2-6 alkynylaminocarbonyl, arylaminocarbonyl, diarylaminocarbonyl, aryl-C 1-6 alkylaminocarbonyl, C 2-6 aryl-alkenylaminocarbonyl, C 2-6 aryl-alkylaminocarbonyl, C 3-7 aryl-cycloalkylaminocarbonyl, heteroarylaminocarbonyl, diheteroarylaminocarbonyl, heteroaryl-alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylaminocarbonyl-C 1-6 alkylarylcarbonyl-C 1-6 alkylarylcarbonyl-C 1-6 alkylaminocarbonyl-C 1 -C 6 -alkyl C2-6 alkynylaminocarbonyl, cycloalkylaminocarbonyl C3-7 heteroaryl-, heteroarilarilaminocarbonilo, heterocyclylaminocarbonyl, diheterocyclylamino-carbonyl, heterocyclyl-C1-6 alkylaminocarbonyl, heterocyclyl-C2-6 alkenylamino-carbonyl, heterocyclyl-C2-6 alkynylaminocarbonyl, heterocyclyl- C3-7 cycloalkylaminocarbonyl, heterociclilarilaminocarbonilo, heterociclilheteroarilamino-carbonyl, C1-6 alkylsulfinyl, C3-7 cycloalkylsulfinyl, C2-6 alkenylsulfinyl, C2-6 alkylsulfinyl, arylsulfinyl, heteroarylsulfinyl, heterocyclylsulfinyl, C1-6 alkylsulfonyl, C3-7 cycloalkylsulfonyl, C2-6 alkenylsulfonyl, alkynylsulfonyl C2- 6, arylsulfonyl, heteroarylsulfonyl, het erocyclylsulfonyl, C1-6 alkylsulfonylamino or arylsulfonylamino; and R 12 represents hydrogen, C 1-6 alkyl, C 3-7 cycloalkyl, C 2-6 alkenyl, C 2-6 alkynyl, acyl, aryl, heteroaryl, heterocyclyl, C 1-6 alkylaminocarbonyl, C 1-6 alkylaminocarbonyl, alkylsulfonyl C1-6, arylsulfonyl or heteroarylsulfonyl; and pharmaceutically acceptable optical isomers, salts, hydrates, solvates and polymorphs of said compound, wherein a compound of formula (2) is suspended in a mixture of ethanol and water and treated with hydrochloric acid, followed by reaction with H2NNHCOOCH3, to provide a compound of formula (3), which is reacted with a compound of formula (4) to provide a compound of formula (5) which is hydrolyzed under acidic conditions to provide a compound of formula (6) which is treated with an amine of formula (7) in the presence of a condensing agent, to provide a compound of formula (1), which is converted, if so desired, into a salt, hydrate, solvate or drug polymorph |
priorityDate | 2006-08-04-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
type | http://data.epo.org/linked-data/def/patent/Publication |
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