- NEW CRTH2 ANTAGONISTS
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The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.
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Page/Page column 142-143
(2013/03/26)
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- NEW CRTh2 ANTAGONISTS
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The present invention relates to compounds of formula (I), to the process for preparing such compounds and to their use in the treatment of a pathological condition or disease susceptible to amelioration by CRTh2 antagonist activity.
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Page/Page column 123-124
(2013/03/26)
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- Amino-Containing Compounds Which Inhibit Memapsin 2 Beta-Secretase Activity and Methods of Use Thereof
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The present invention provides novel beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer's disease.
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Page/Page column 19
(2008/12/05)
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- BICYCLIC COMPOUNDS WHICH INHIBIT BETA-SECRETASE ACTIVITY AND METHODS OF USE THEREOF
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The present invention provides bicyclic beta-secretase inhibitors and methods for their use, including methods of treating of Alzheimer’s disease.
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Page/Page column 59
(2010/10/20)
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- Nitropyrazoles: XII. Transformations of the 4-methyl group in 1,4-dimethyl-3,5-dinitropyrazole and cyclization of the transformation products
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A preparative procedure for the synthesis of 1,4-dimethyl-3,5- dinitropyrazole by nitration of 1,4-dimethylpyrazole was developed. The reaction of 1,4-dimethyl-3,5-dinitropyrazole with dimethoxymethyl-(dimethyl)amine (N,N-dimethylformamide dimethyl acetal) gave (E)-N,N-dimethyl-2-(1-methyl-3,5- dinitropyrazol-4-yl)ethenylamine. Acid hydrolysis of the latter afforded (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde, and the reaction with sodium nitrite in hydrochloric acid led to formation of 2-hydroxymino-2-(1-methyl-3,5- dinitropyrazol-4-yl)acetaldehyde. The corresponding O-methyloxime and phenylhydrazone reacted with K2CO3 to give 6-methyl-4-nitropyrazolo[4,3-d]isoxazole-3-carbaldehyde O-methyloxime and 1-methyl-3-nitro-4-(2-phenyl-2H-1,2,3-triazol-4-yl)pyrazol-5-ol, respectively. Treatment of (1-methyl-3,5-dinitropyrazol-4-yl)-acetaldehyde with benzenediazonium chloride gave (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde phenylhydrazone which underwent intramolecular cyclization with replacement of the 5-nitro group by the action of K2CO3 in acetonitrile; in the reaction with K2CO3 in ethanol, the 5-nitro group was replaced by ethoxy.
- Zaitsev,Dalinger,Starosotnikov,Kachala,Strelenko,Shkineva,Shevelev
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p. 1507 - 1515
(2007/10/03)
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- Method for producing 1 substituted 5-chloro-4 methly pyrazoles
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The present invention relates to a process for preparing 1-substituted 5-chloro-4-methylpyrazoles of the general formula I with the meaning for R stated in claim 1, in which a 4-methylpyrazole of the formula II is reacted with chlorine, the resulting mixture of monochlorinated and dichlorinated product is fractionated by distillation, and subsequently the dichlorinated compound is dehalogenated to compound II and returned to the reaction with chlorine.
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- N-alkylation method of pyrazole
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An N-alkylation method of pyrazole in which (III) is produced from (I) and (II), which is characterized by using a crystalline aluminosilicate or a crystalline aluminophosphate as a catalyst: STR1 wherein each of R1, R2 and R3 represents hydrogen, alkyl, alkenyl or phenyl, R represents alkyl and Q represents hydrogen, alkyl or COOR. This is an industrially markedly useful method, because (III) can be obtained with a high yield under mild reaction conditions, and by-products including salts are not at all formed.
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- Process for preparing N-substituted pyrazoles
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A process for the preparation of an N-alkyl- or N-phenylalkyl-substituted pyrazole I by reacting the corresponding N-unsubstituted pyrazole II with an alcohol III of the formula R1 --OH where R1 is the same alkyl or phenylalkyl group to be added to the unsubstituted nitrogen group --NH-- of the pyrazole reactant. Both of the reactants, i.e. the pyrazole II and alcohol III compounds, are catalytically reacted in the liquid phase in a molar ratio of from 0.001:1 to 1:1, at temperatures of 50°-400° C. and under a subatmosheric pressure of from 0.8 bar up to a superatmospheric pressure of 250 bar. The catalyst required for this liquid phase reaction is selected as being at least one or more non-heterogeneous acid catalysts, their alkyl esters or their acid anhydrides.
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- N-alkylation of heterocyclic, aromatic amines
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A process for producing a heterocyclic tertiary amine of the formula (III): STR1 wherein A is a nitrogen atom or C-R5, B is a nitrogen atom or C-R6, is a single bond or a double bond, and each of R1, R2, R3, R4, R5 and R6 which may be the same or different, is a hydrogen atom, an acyl group, a halogen atom, a cyano group, etc., provided that two of R1, R2, R3 and R4 may together form a 3-membered, 4-membered, 5-membered or 6-membered aliphatic ring, a heterocyclic rig or aromatic ring, and R7 is a C1-6 alkyl group which may be substituted, etc., which process comprises reacting a heterocyclic secondary amine of the formula (I): STR2 wherein A, B, , R1, R2, R3 and R4 are as defined above, with an alkylating agent of the formula (II): wherein R7 is as defined above, and X is a hydroxyl group, a halogen atom, a OSO3 R7 group, a OSO2 R7 group, a OCO2 R7 group, a OCOR7 group, a OP(O)(OR7) group, a OP(O)O(R7)2 group or an amino group, in the presence of a catalyst of Group VIII of the Periodic Table.
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