- Synthesis of butanoic acid 4,4'-[(4E, 6Z, 9Z-pentadecatrien-2-ynylidene)]-bis with leukotriene-like activity: Novel acetylenic acetals and dithioacetals as antagonists of leukotriene-C4
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A selective exchange reaction of a symmetrical acetal with protected cysteine readily provided two hemi-thioacetals related to leukotriene-E4. Use of acetylene-bis-(diethyl acetal) led to a facile synthesis of the title compound. Its correspond
- Saksena,Green,Mangiaracina,et al.
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- Soluble and polymer-supported 2- and 3-benzylated furans for the preparation of α,β-ethylenic carbonyl compounds
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Soluble and polymer-supported 2- and 3-benzylated furans were subjected to a sequence involving a Diels-Alder reaction with α,β-acetylenic carbonyl compounds, a Michael addition, and a subsequent retro-Diels-Alder reaction to yield olefinic compounds. On solid support, this traceless strategy is advantageous since pure compounds were released in the thermal cycloreversion step. The fur-2-ylated resin allowed a highly diastereoselective synthesis.
- Albert, Sébastien,Soret, Adrien,Blanco, Luis,Deloisy, Sandrine
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p. 2888 - 2900
(2007/10/03)
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- Aminomethylpyrimidines as allosteric enhancers of the GABAB receptors
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The present invention relates to compounds of formula whereinX is —S— or —NH—; R3/R4 together with the N-atom to which they are attached form a non aromatic 5, 6 or 7 membered ring, which optionally contains in addition to the N-atom one additional heteroatom selected from the group consisting of O, S and N, and wherein the ring is optionally substituted by hydroxy, lower alkyl, lower alkoxy, —NR2, —CONR2, —CO-lower alkyl or benzyl; or R3/R4 form together with the N-atom to which they are attached a heterocyclic ring system, containing two or three rings and which optionally contains one or two additional heteroatoms selected from the group consisting of N and O and which has no more than 20 carbon atoms; and R, R1, R2, and R5 are as defined herein and to pharmaceutically suitable acid addition salts thereof. It has been found that the compounds of the invention are active on the GABAB receptor and therefore are useful for the treatment of anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders and gastro-intestinal disorders.
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Page/Page column 13
(2010/02/13)
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- 4- (SULFANYL-PYRIMIDIN-4-YLMETHYL) -MORPHOLINE DERIVATIVES AND RELATED COMPOUNDS AS GABA RECEPTOR LIGANDS FOR THE TREATMENT OF ANXIETY, DEPRESSION AND EPILEPSY
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The present invention relates to compounds of Formula (I) wherein X is-S-or-NH-; R1 is alkyl, alkenyl, arylalkyl, arylalkenyl or aryl-O-alkyl, wherein the aryl groups are optionally substituted by one or more substituents, selected from the group consisting of lower alkyl, lower alkoxy, halogen or lower halogen-alkyl; R2 is hydrogen, lower alkyl or cycloalkyl; R3 /R4 may form together with the N-atom to which they are attached a non aromatic5, 6 or 7 membered ring, which may contain in addition to the N-atom one additional heteroatom selected from the group consisting of O, S or N, and wherein the ring is optionally substituted by hydroxy, lower alkyl, lower alkoxy,-NR2,-CONR2,-CO-lower alkyl or benzyl; or may form together with the N-atom to which they are attached a heterocyclic ring system, containing at least two rings and which may contain one or two additional heretoatoms, selected from the group consisting of N or O; R is hydrogen or lower alkyl; R5 is hydrogen or lower alkyl; and to pharmaceutically suitable acid addition salts thereof. It has been found that the compounds are active on the GABAB receptor and therefore useful for the treatment of anxiety, depression, epilepsy, schizophrenia, cognitive disorders, spasticity and skeletal muscle rigidity, spinal cord injury, multiple sclerosis, amyotrophic lateral sclerosis, cerebral palsy, neuropathic pain and craving associated with cocaine and nicotine, psychosis, panic disorder, posttraumatic stress disorders or gastro-intestinal disorders.
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Page/Page column 25
(2010/02/14)
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- Synthese regioselective par voie organometallique d'amines primaires propargyliques γ-fonctionnelles et applications
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Reactive organozincs obtained from allylic and propargylic bromides regioselectively react with the N-trimethylsilylaldimine prepared in situ from the diethylmonoacetal of acetylenedicarbaldehyde and lead to unsatured γ-functional primary amines which possess many synthetic uses.
- Courtois, Gilles,Desre, Valerie,Miginiac, Leone
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p. 279 - 292
(2007/10/03)
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Procedures for isolating acetylenedicarbaldehyde (ADCA) 1 in the pure state, or for obtaining this unstable compound in diluted aprotic solutions (CH2Cl2, CCl4, toluene) are detailed. They are based on the acidolysis of it
- Gorgues,Stephan,Belyasmine,Khanous,Co
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p. 2817 - 2826
(2007/10/02)
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- VERSATILITE DE REACTIVITE DE L'ACETYLENE DICARBALDEHYDE ET DES ALDEHYDES α-ACETYLENIQUES A L'EGARD DES DIENES CONJUGUES CYCLIQUES ET HETEROCYCLIQUES EN MILIEU ACIDE
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The preparation of acetylenedicarbaldehyde 1 and the corresponding mono acetal 2 is described.A comparison of their reactivity with other α-acetylenic aldehydes RCCCHO 3 to 9 towards conjugated cyclic or heterocyclic dienes is presented.Under neutral conditions, the only expected Diels-Alder adducts I are formed.Under acidic conditions (HCO2H, CF3CO2H or eventually AcOH) they afford the only Diels-Alder adduct I when the cyclodiene does not present any aromatic character, and, on the opposite case, the Michael adducts II with more or less important amounts of I; starting from furan, a third pathway could also be observed dealing with t he formation of the double electrophilic substitution compounds III.The mechanisms are discussed and particularly, a common dipolar intermediate P is suggested to account for the competitive formation of I and II.
- Gorgues, A.,Simon, A.,Coq, A. Le,Hercouet, A.,Corre, F.
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p. 351 - 370
(2007/10/02)
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