- Intermolecular cyclocondensation of arylchloropyruvates in the synthesis of 2,3-dihydrofuran-3,5-dicarboxylic acid derivatives
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Methyl arylchloropyruvates undergo intermolecular self-condensation in the presence of a catalytic amount of a base under high-temperature conditions (~250°C) with the formation of 3,4-diaryl-2-oxo-2,3-dihydrofuran-3,5-dicarboxylic acid derivatives.
- Mamedov,Khafizova,Zamaletdinova,Dobrynin,Litvinov,Sinyashin
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- SUBSTITUTED 2-AZABICYCLO[3.1.1]HEPTANE AND 2-AZABICYCLO[3.2.1]OCTANE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
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There is provided a compound of formula (I), wherein L1 to L3, R1 to R4, X, A and B have meanings given in the description, and pharmaceutically acceptable salts, solvates and prodrugs thereof, which compounds are useful as antagonists of the orexin-1 and orexin-2 receptors or as selective antagonists of the orexin-1 receptor, and thus, in particular, in the treatment or prevention of inter alia substance dependence, addiction, anxiety disorders, panic disorders, binge eating, compulsive disorders, impulse control disorders, cognitive impairment and Alzheimer's disease.
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Page/Page column 98-99; 101
(2019/03/17)
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- OXAZOLE AND THIAZOLE DERIVATIVES AS ALX RECEPTOR AGONISTS
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The invention relates to oxazole and thiazole derivatives of formula (I), wherein A, E, X, R1 and R2 are as defined in the description, their preparation and their use as pharmaceutically active compounds.
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Page/Page column 35
(2012/05/20)
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- 2-AZA-BICYCLO[3.3.0]OCTANE DERIVATIVES
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The invention relates to 2-aza-bicyclo[3.3.0]octane derivatives of Formula (I) wherein A, B, and R1 are as described in the description, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.
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Page/Page column 11
(2011/02/15)
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- PIPERIDINE AND PYROOLIDINE COMPOUNDS
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The invention relates to piperidine and pyrrolidine compounds of formula (I) wherein A, B, n and X are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds use as medicaments, especially as orexin receptor antagonists.
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Page/Page column 12
(2011/04/13)
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- THIAZOLIDINE COMPOUNDS AS OREXIN RECEPTOR ANTAGONISTS
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The invention relates to thiazolidine derivatives of the formula (I) wherein A, B, and R1 are as described in the description, to salts, especially pharmaceutically acceptable salts, of such compounds and to their use as medicaments, especially
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Page/Page column 26
(2011/05/08)
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- 1,2-DIAMIDO-ETHYLENE DERIVATIVES AS OREXIN ANTAGONISTS
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The invention relates to 1,2-diamido-ethylene derivatives of the formula (I) wherein R1, R2, R3, and A are as described in the description and their use as medicaments, especially as orexin receptor antagonists.
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Page/Page column 23; 24
(2011/11/06)
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- PHENETHYLAMIDE DERIVATIVES AND THEIR HETEROCYCLIC ANALOGUES
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The invention relates to novel phenethylamide derivatives and their heterocyclic analogues of formula (I), wherein A, B, R1, R2 and R3 are as described in the application, and to the use of such compounds, or of pharmaceut
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Page/Page column 82
(2010/04/30)
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- THIAZOLIDINE COMPOUNDS AS OREXIN RECEPTOR ANTAGONISTS
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The invention relates to thiazolidine derivatives of the formula (I) wherein A, B, and R1 are as described in the description, to salts, especially pharmaceutically acceptable salts, of such compounds and to their use as medicaments, especially
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Page/Page column 52
(2010/04/03)
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- THIAZOLIDINE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
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The invention relates to novel thiazolidine derivatives of the formula (I) wherein A and R1 are as described in the description and their use as medicaments, especially as orexin receptor antagonists.
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Page/Page column 20-21
(2010/05/13)
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- TRANS-3-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES
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The invention relates to novel trans-3-aza-bicyclo[3.1.0]hexane derivatives of formula (I), wherein A, B, n and R1 are as described in the description, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.
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Page/Page column 50; 52
(2009/03/07)
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- 2-AZA-BICYCLO[3.3.0]OCTANE DERIVATIVES
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The invention relates to 2-aza-bicyclo[3.3.0]octane derivatives of Formula (I) wherein A, B, and R1 are as described in the description, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.
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Page/Page column 22
(2009/03/07)
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- 2-AZA-BICYCLO[2.2.1]HEPTANE DERIVATIVES
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The invention relates to novel 2-aza-bicyclo[2.2.1]heptane derivatives of formula (I), wherein A, B, n and R1 are as described in the description, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as m
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Page/Page column 40-41
(2009/10/18)
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- PIPERIDINE AND PYRROLIDINE COMPOUNDS
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The invention relates to piperidine and pyrrolidine compounds of formula (I) wherein A, B, n and X are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds use as medicaments, especially as orexin receptor antagonists.
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Page/Page column 25
(2009/12/05)
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- 3-AZA-BICYCLO[3.3.0]OCTANE COMPOUNDS
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The invention relates to 3-aza-bicyclo[3.3.0]octane derivatives of the formula (I) wherein R1, R2, R3, and A are as described in the description and their use as orexin receptor antagonists.
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Page/Page column 35
(2009/03/07)
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- 1,2-DIAMIDO-ETHYLENE DERIVATIVES
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The invention relates to 1,2-diamido-ethylene derivatives of the formula (I) NHNR 3 OAOR 1 R 2 (I) wherein R1, R 2, R 3, and A are as described in the description and their use as medicaments, especially as orexin receptor
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Page/Page column 54
(2009/04/25)
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- 2-AZA-BICYCLO[3.1.0]HEXANE DERIVATIVES
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The invention relates to novel 2-aza-bicyclo[3.1.0]hexane derivatives of Formula (I) wherein A, B, n and R1 are as described in the description, and to the use of such compounds, or of pharmaceutically acceptable salts of such compounds, as medicaments, especially as orexin receptor antagonists.
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Page/Page column 49
(2008/12/07)
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- 2-CYCLOPROPYL-THIAZOLE DERIVATIVES
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The invention relates to selected 2-cyclopropyl-thiazole derivatives of the formula (I) wherein B, Y and R1 are as described in the description; to salts and especially pharmaceutically acceptable salts thereof, and to the use of such compounds use as medicaments, especially as orexin receptor antagonists.
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Page/Page column 44
(2009/01/20)
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- Synthesis of oxazolidines using DMSO/P4O10 as a formaldehyde equivalent
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Compounds containing a substituted oxazolidine ring were prepared in excellent yields in two steps from cis or trans 3-phenylglycidate. When an electron donating amine was used in the nucleophilic opening of an epoxide, treatment of the resulting β-amino-
- Wang, Jianmei,Rochon, Fernande D.,Yang, Yan,Hua, Ling,Kayser, Margaret M.
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p. 1115 - 1123
(2008/02/08)
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- Substituted benzaldehydes in the darzens condensation with alkyl dihaloacetates
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The Darzens reaction of dihaloacetic acid esters with aromatic aldehydes produces either arylhaloglycidic or arylhalopyruvic esters depending on the nature of the substituent in the aromatic ring. Alkyl p- methoxyphenylchloropyruvates undergo spontaneous intermolecular cyclocondensation to form pyranone or furanone derivatives depending on the character of the alkyl fragment.
- Mamedov,Berdnikov,Tsuboi,Hamamoto,Komiyama,Gorbunova,Gubaidullin,Litvinov
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p. 1455 - 1463
(2007/10/03)
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- Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)
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Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).
- Hamamoto, Hiromi,Mamedov, Vakhid A.,Kitamoto, Makiko,Hayashi, Nobuyuki,Tsuboi, Sadao
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p. 4485 - 4497
(2007/10/03)
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- Dimethyl dichloromalonate as a new synthetic equivalent of methyl dichloroacetate in the Darzens condensation
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Dimethyl dichloromalonate reacts with aldehydes in the presence of sodium methoxide to form α-chloropyruvates, α-chloroglycidates, or α,α-dichlorohydrins, depending on the nature of the aldehyde. - Keywords: dimethyl dichloromalonate, Darzens reaction, α-
- Berdnikov, E. A.,Mamedov, V. A.
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p. 1484 - 1485
(2007/10/02)
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- Dimethyl dichloromalonatc as a new synthetic equivalent of methyl dichloroacetate in the darzens condensation
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Dimethyl dichloromalonate reacts with aldehydes in the presence of sodium methoxide to form α-chloropyruvates, α-chloroglycidates, or α,α-dichlorohydrins, depending on the nature of the aldehyde.
- Berdnikov,Mamedov
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p. 1484 - 1485
(2015/04/14)
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- Regioselective ring opening of 3-aryl-2-cyano-2-(methoxycarbonyl)oxiranes with metal halides and silica-gel-supported metal halides. Synthesis of substituted but-3-en-4-olides.
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Regioselective ring opening of 3-aryl-2-cyano-2-(methoxycarbonyl)oxiranes 1 with transition metal halides (copper(II) chloride, copper (II) bromide, zinc bromide, cobalt chloride and ferric chloride) and silica-gel-supported metal halides gave methyl 3-aryl-2-cyano-3-halo-2-hydroxypropanoates 5, 6 and methyl 3-aryl-3-halo-2-oxopropanoates 2, 3.The reaction of 1 in chlorobenzene under reflux with silica-gel-supported copper (II) halides gave but-3-en-4-olides 4.Key Words: methyl 3-aryl-2-cyano-3-halo-2-hydroxypropanoates; methyl 3-aryl-3-halo-2-oxopropanoates; but-3-en-4-olides.
- Brine, N.,Foucaud, A.
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p. 620 - 624
(2007/10/02)
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- REACTION OF METHYL DICHLOROACETATE WITH SUBSTITUTED BENZALDEHYDES UNDER THE CONDITIONS OF THE DARZENS CONDENSATION
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We have found that condensation of methyl dichloroacetate (1) with benzaldehyde, p-chloro- and p-bromobenzaldehyde in t-BuOH in the presence of t-BuOK yields methyl 3-aryl-3-chloro-2-oxopropionates (3-5).In the case of nitrobenzaldehydes the reaction prod
- Mamedov, V. A.,Nuretdinov, I. A.
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p. 1690 - 1692
(2007/10/02)
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