68064-69-7

Usage

Uses

Used in Agricultural Industry:
Z-2-(2,3-Dichlorophenyl)methylene-3-oxobutanoic acid methyleater is used as an agricultural herbicide for controlling weeds and unwanted plants in various crop fields. It functions by inhibiting the growth of certain plant species, ultimately leading to their death. This helps to protect crops from competition and improve yield.
However, it is crucial to handle and use this chemical with caution due to its potential harmful effects if ingested, inhaled, or comes into contact with the skin. Proper safety measures and guidelines should be followed to minimize risks associated with its use.

InChI:InChI=1/C12H10Cl2O3/c1-7(15)9(12(16)17-2)6-8-4-3-5-10(13)11(8)14/h3-6H,1-2H3/b9-6-

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 6334-18-5 2,3-dichlorobenzylaldehyde 
• 110-89-4 piperidine 

Downstream Products

• 72509-76-3 ethyl methyl 1,4-dihydro-2,6-dimethyl-4(2,3-dichlorophenyl)-3,5-pyridinedicarboxylate 
• 108931-67-5 4-(2 3-Dichlorophenyl)-1 4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-5-pyrimidinecarboxylic acid, methyl ester 
• 108931-53-9 1,4-dihydro-2-methoxy-6-methyl-4-(2,3-dichlorophenyl)-5-pyrimidinecarboxylic acid, methyl ester 
• 176089-73-9 Methyl 5-cyano-4-(2,3-dichlorophenyl)-2-methyl-6-N-methylamino-1,4-dihydropyridine-3-carboxylate 
• 88150-46-3 2-(2-azidoethoxy)methyl-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine 
• 88150-49-6 2-(2-azidoethoxy)methyl-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine 
• 111199-76-9 2-(cyanoimino)-6-(2,3-dichlorophenyl)-3,6-dihydro-4-methyl-5-pyrimidinecarboxylic acid, methyl ester 
• 113607-39-9 1,4-Dihydro-2,6-dimethyl-3-methoxycarbonyl-4-(2,3-dichlorophenyl)-5-(2-phthalimidoethoxy)carbonylpyridine 
• 1376615-40-5 (Z)-methyl 3-(2,3-dichlorophenyl)-2-(2-methyl-1,3-dioxolan-2-yl)acrylate 
• 1376615-47-2 (E)-ethyl 4-(2,3-dichlorophenyl)-5-((hydroxyimino)methyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate 
• 1376615-46-1 (E)-ethyl 5-((allyloxyimino)methyl)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate 
• 1376615-45-0 (1E,2E)-2-(2,3-dichlorobenzylidene)-3-oxobutanal O-allyl oxime 
• 1376615-44-9 (1E,2E)-3-(2,3-dichlorophenyl)-2-(2-methyl-1,3-dioxolan-2-yl)acrylaldehyde O-allyl oxime 
• 1376615-43-8 (1E,2E)-3-(2,3-dichlorophenyl)-2-(2-methyl-1,3-dioxolan-2-yl)acrylaldehyde oxime 

Relevant academic research and scientific papers

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

PROCESS FOR THE PREPARATION OF 4 -SUBSTITUTED -1, 4-DIHYDROPYRIDINES

4-Substituted-l,4-dihydropyridines of formula I are prepared by a cycloaddition reaction in which the cyclization is driven to completion at ambient temperature optionally in water without any catalyst. For exemplary purposes, the invention is described in particular detail with respect to the preparation of felodipine of formula II. Felodipine, a vasodilator, is prepared by a cycloaddition reaction of alkyl 3- aminocrotonate with dichlorobenzylidene under reaction conditions whereby the product crystallizes out of the reaction solution and may be directly isolated by filtration.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

Process to prepare 1,4-dihydropyridine intermediates and derivatives thereof

An improved catalyst is disclosed for a process involving the preparation of benzylidene intermediates useful in the preparation of 1,4-dihydropyridine compounds and derivatives thereof useful as medicines such as for example felodipine. This is accomplished by the condensation of an aldehyde and an acetoacetate in the presence of a novel catalyst system that includes a pyridyl carboxylic acid and a secondary amine. It has been found that through the use of the present invention the purity and yield of the desired isomer of the benzylidene intermediate can be maximized, thus avoiding the requirement of additional purification steps. The use of these intermediates can then be further reacted to form the required dihydropyridines, again having a very high purity and yield compared with the prior art.

USE OF 1,2-BRIDGED 1,4-DIHYDROPYRIDINES AS MEDICAMENTS

The present invention relates to the new use of 1,2-bridged 1, 4-dihydropyridines which are known in some cases, of the general formula (I) STR1 in which R 1 to R 4 and a have the meaning indicated in the description, processes for their preparation and t

Synthesis of 1,4-dihydro-2,6-dimethyl-4-(substituted phenyl)-5-N-methylaminocarbonyl-pyridine-3-carboxylate

Michael addition of β-amino-N-methylcrotonamide to aralkylideneacetoacetic acid ester is followed by ring closer to give novel 4-aryl-1,4-dihydro-2,6-dimethyl-5-N-methylaminocarbonylpyridine-3-carboxylates (5).

Process for the preparation of 1,4-dihydropyridinedicarboxylic esters

In the preparation of a 1,4-dihydropyridine of the formula STR1 in which R is a phenyl radical which is optionally substituted once or twice by nitro and/or chlorine, R1 is a C1 -C4 -alkyl radical which is optionally substituted by a C1 -C4 -alkoxy group, and R2 is a C1 -C12 -alkyl radical which is optionally substituted by a C1 -C4 -alkoxy group, a trifluoromethyl group or the radical (C6 H5 CH2) (CH3)N, by preparing an ylidene compound of the formula STR2 and reacting such ylidene compound with an enamine compound of the formula STR3 the improvement which comprises preparing the ylidene compound by reaction of a ketocarboxylic ester of the formula STR4 with an aldehyde of the formula RCHO, in a solvent in the presence of a catalytic amount of any acetate salt of an amine, at a temperature from about -10° C. up to 100° C. The products symmetrical or unsymmetrical, are produced in high yield and purity.