Title:
4H-1,2,4-TRIAZIN-5-ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE AS ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTORS
Document Type and Number:
WIPO Patent Application WO2006111662
Kind Code:
A3
Abstract:
The invention relates to triazine derivatives of general formula (I) in which R1 represents a heteroaryl group or aryl group; R2 represents a hydrogen atom or a group (C1-C4) alkyl; R3 represents a group -(CH2)n-NR4R5in which n is equal to 2, 3 or 4 and R4 and R5, independent of one another, represent a (C1-C4) alkyl group or (C3-C7) cycloalkyl, or R4 and R5, together with the nitrogen atom that carries them, form a (C3-C9) heterocycloalkyl group or; R3 represents a group -(CH2)m-NR4R5 in which m is equal to 0, 1, 2, 3 or 4, and; R6 represents a (C3-C9) heterocycloalkyl group comprising at least one nitrogen atom and bound to the triazine nucleus by a carbon atom; R2 and R3, together with the nitrogen atom carrying them, form a (C5-C9) heterocycloalkyl comprising 2 nitrogen atoms; in the form of a base or of an acid addition salt, as well as in the form of a hydrate or solvate. The invention also relates to a method for preparing these triazine derivatives and their use as ligands of a7 nicotinic acetylcholine receptors.
Inventors:
BENEDETTI YANNICK (FR)
BOHME ANDREES (FR)
GENEVOIS-BORELLA ARIELLE (FR)
TOUYER GAETAN (FR)
ZHANG JIDONG (FR)
BOHME ANDREES (FR)
GENEVOIS-BORELLA ARIELLE (FR)
TOUYER GAETAN (FR)
ZHANG JIDONG (FR)
Application Number:
PCT/FR2006/000887
Publication Date:
November 30, 2006
Filing Date:
April 21, 2006
Export Citation:
Assignee:
AVENTIS PHARMA SA (FR)
BENEDETTI YANNICK (FR)
BOHME ANDREES (FR)
GENEVOIS-BORELLA ARIELLE (FR)
TOUYER GAETAN (FR)
ZHANG JIDONG (FR)
BENEDETTI YANNICK (FR)
BOHME ANDREES (FR)
GENEVOIS-BORELLA ARIELLE (FR)
TOUYER GAETAN (FR)
ZHANG JIDONG (FR)
International Classes:
C07D403/04; C07D253/06; C07D405/04; C07D409/04; C07D453/02
Domestic Patent References:
| WO2003029252A1 | 2003-04-10 |
Other References:
PATENT ABSTRACTS OF JAPAN vol. 2002, no. 05 3 May 2002 (2002-05-03)
RIED, WALTER ET AL: "Nucleophilic reactions on chloro-N-(2-oxoacyl)formamidines", LIEBIGS ANNALEN DER CHEMIE , (2), 141-8 CODEN: LACHDL; ISSN: 0170-2041, 1988, XP001149027
LAVERGNE, JEAN PIERRE ET AL: "Research in the azabenzodiazepine series. IV. 1-(3'- Triazinyl)ethylenediamines, synthetic intermediates for 7,8,9,10-tetrahydro-(2H)(6H)-as-triazino[2,3-c]-1,3,5-triazepines", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE , (11-12, PT. 2), 1827-8 CODEN: BSCFAS; ISSN: 0037-8968, 1976, XP009056964
LALEZARI, IRADJ: "1,2,4-Triazines. VIII. The synthesis of 1,2,4-triazino[2,3- e]pyrazolo[1,5-a]-1,3,5-triazines and 1,2,4-triazino[4,3-e]pyrazolo[1,5-a]- 1,3,5-triazines", JOURNAL OF HETEROCYCLIC CHEMISTRY , 13(6), 1249-51 CODEN: JHTCAD; ISSN: 0022-152X, 1976, XP002353864
BURCH, HOMER A.: "Nitrofuryl heterocycles. X. Analogs of 6-(5-nitro-2-furyl)-as-triazine- 3,5(2H,4H)-dione", JOURNAL OF MEDICINAL CHEMISTRY , 13(2), 288-91 CODEN: JMCMAR; ISSN: 0022-2623, 1970, XP001119262
RIED, WALTER ET AL: "Nucleophilic reactions on chloro-N-(2-oxoacyl)formamidines", LIEBIGS ANNALEN DER CHEMIE , (2), 141-8 CODEN: LACHDL; ISSN: 0170-2041, 1988, XP001149027
LAVERGNE, JEAN PIERRE ET AL: "Research in the azabenzodiazepine series. IV. 1-(3'- Triazinyl)ethylenediamines, synthetic intermediates for 7,8,9,10-tetrahydro-(2H)(6H)-as-triazino[2,3-c]-1,3,5-triazepines", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE , (11-12, PT. 2), 1827-8 CODEN: BSCFAS; ISSN: 0037-8968, 1976, XP009056964
LALEZARI, IRADJ: "1,2,4-Triazines. VIII. The synthesis of 1,2,4-triazino[2,3- e]pyrazolo[1,5-a]-1,3,5-triazines and 1,2,4-triazino[4,3-e]pyrazolo[1,5-a]- 1,3,5-triazines", JOURNAL OF HETEROCYCLIC CHEMISTRY , 13(6), 1249-51 CODEN: JHTCAD; ISSN: 0022-152X, 1976, XP002353864
BURCH, HOMER A.: "Nitrofuryl heterocycles. X. Analogs of 6-(5-nitro-2-furyl)-as-triazine- 3,5(2H,4H)-dione", JOURNAL OF MEDICINAL CHEMISTRY , 13(2), 288-91 CODEN: JMCMAR; ISSN: 0022-2623, 1970, XP001119262
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