35594-15-1Relevant academic research and scientific papers
METHYL 2-METHYL-5-OXO-1,4,5,7-TETRADHYDROFURO[3,4-b]PYRIDINE-3-CARBOXYLATE COMPOUNDS AS CAV1.2 ACTIVATORS
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Paragraph 0217-0220, (2021/12/29)
The present disclosure provides for a compound according to formula (I) or a pharmaceutically acceptable salt thereof as Cav1.2 activators for the treatment of schizophrenia, bipolar disorder, major depressive disorder, substance use disorder, ADHD, Phelan-McDermid Syndrome, autism spectrum disorder, multiple sclerosis, frontotemporal dementia, Alzheimer's disease, Brugada Syndrome, Short QT syndrome, and early repolarization syndrome.
METHYL(R)-2-(FLUOROMETHYL)-5-OXO-4-PHENYL-4,5,6, 7-TETRAHYDRO-1H-CYCLOPENTA[B]PYRIDINE-3-CARBOXYLATE AND METHYL(R)-2-(FLUOROMETHYL)-5-OXO-4-PHENYL-1,4,5,7-TETRAHYDROFURO[3,4-B]PYRIDINE-3-CARBOXYLATE USED AS ACTIVATORS OF CAV1.2
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Page/Page column 31, (2022/01/05)
The invention relates to a compound according to formula (I) or a pharmaceutically acceptable salt thereof used as activators of CaV1.2 for the treatment of schizophrenia, bipolar disorder, major depressive disorder, ADHD, Phelan-McDermid syndrome, autism spectrum disorder, multiple sclerosis, frontotemporal dementia, Alzheimer's disease, Brugada syndrome, short QT syndrome or early repolarization syndrome.
Synthesis of diverse acyclic precursors to pyrroles for studies of prebiotic routes to tetrapyrrole macrocycles
Chandrashaker, Vanampally,Ptaszek, Marcin,Taniguchi, Masahiko,Lindsey, Jonathan S.
, p. 8786 - 8808 (2016/10/13)
A chemical model for the origin of tetrapyrrole macrocycles under prebiotic conditions entails the condensation of acyclic dicarbonyl compounds and α-aminoketones to form pyrroles that are equipped for subsequent self-condensation. Development and exploration of the scope of the chemical model (including combinatorial reactions, studies of the effects of structurally defective substrates, and reactions in aqueous or organic media) have relied on the availability of diverse starting materials prepared by traditional chemical synthesis methods. Here the synthesis of all acyclic dicarbonyl compounds and α-aminoketones used in the prior prebiotic model studies is described. There are five sets of acyclic dicarbonyl compounds including (i) β-ketoesters bearing diverse 4-substituents, (ii) levulinic acid derivatives bearing selected 5-substituents (i.e., analogues of δ-aminolevulinic acid, ALA), (iii) meso-substituted β-ketoesters, (iv) meso-substituted β-diketones that contain one 4-substituent, and (v) hybrid molecules that contain both the β-ketoacyl unit and the levulinic acid skeleton (or homologue thereof). A variety of α-aminoketones (homologues of ALA) also have been prepared. Altogether, the synthesis of 53 compounds is described, encompassing 28 new compounds as well as 25 known compounds that have been more fully characterized or prepared via alternative routes. The ability to convert selected acyclic compounds directly via pyrroles to porphyrinogens in a single-flask process may also prove useful in mainstream syntheses of diverse tetrapyrroles regardless of possible prebiotic relevance.
Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates
Pradhan, Tapas R.,Mendhekar, Kishor L.,Mohapatra, Debendra K.
, p. 5517 - 5531 (2015/06/16)
The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding β-keto esters. The reaction tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. 18O labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.
DRUG DERIVATIVES
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Paragraph 0252; 0255, (2013/09/12)
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.
DRUG DERIVATIVES
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Page/Page column 81, (2012/05/31)
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.
Ru-catalyzed asymmetric hydrogenation of γ-heteroatom substituted β-keto esters
Fan, Weizheng,Li, Wanfang,Ma, Xin,Tao, Xiaoming,Li, Xiaoming,Yao, Ying,Xie, Xiaomin,Zhang, Zhaoguo
experimental part, p. 9444 - 9451 (2012/01/13)
A series of enantiomerically pure γ-heteroatom substituted β-hydroxy esters were synthesized with high enantioselectivities (up to 99.1% ee) by hydrogenation of γ-heteroatom substituted β-keto esters in the presence of Ru-(S)-SunPhos catalyst. These asymmetric hydrogenations provide key building blocks for a variety of naturally occurring and biologically active compounds.
Latent inhibitors part 11. The synthesis of 5-spirocyclopropyl dihydroorotic acid
Husbands, Stephen,Fraser, William,Suckling, Colin J.,Wood, Hamish C. S.
, p. 865 - 870 (2007/10/02)
Approaches to the synthesis of 5-spirocyclopropyldihydroorotic acid are described. Difficulties were encountered in the lack of reactivity of diethyl 2-oxobutandicarboxylate and its derivatives towards cyclopropanation. Potential intermediates were prepar
Enzymatic Synthesis of Optically Active 2-Carbamoyloxymethyl-1,4-dihydropyridines, (R)-(+)- and (S)-(-)-NB 818
Ebiike, Hirosato,Maruyama, Kaori,Achiwa, Kazuo
, p. 1153 - 1156 (2007/10/02)
Racemic dihydropyridines were resolved by enzyme-catalyzed hydrolysis in an organic solvent saturated with water.The chiral derivatives obtained were converted to (S)- and (R)-NB 818.
Process for the preparation of 4-acyloxy-3-oxo-butyric acid esters
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, (2008/06/13)
A process for the preparation of a 4-acyloxy-3-oxo-butyric acid ester of the formula STR1 in which R1 is alkyl with up to 4 C atoms, and R2 is alkyl with up to 4 C atoms and optionally substituted by halogen, hydroxyl, alkoxy or phenyl, or is aryl, which comprises reacting a 4-halogenobutyric acid ester of the formula STR2 in which X is chlorine or bromine, with a carboxylic acid of the formula STR3 in the presence of acid-trapping agent in an organic solvent at a temperature of between 0° and 170° C.
