- Polymorphism of dehydro-aripiprazole, the active metabolite of the antipsychotic drug aripiprazole (abilify)
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Crystal form exploration of dehydro-aripiprazole (dAPZ), the active metabolite of the antipsychotic drug aripiprazole (APZ), elucidated five polymorphs (I, II, III, IV, and V), two methanol solvates, and a monohydrate. The forms were characterized by ther
- Zeidan, Tarek A.,Trotta, Jacob T.,Chiarella, Renato A.,Oliveira, Mark A.,Hickey, Magali B.,Almarsson, Oern,Remenar, Julius F.
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- Oxidative Aromatization of 3,4-Dihydroquinolin-2(1 H)-ones to Quinolin-2(1 H)-ones Using Transition-Metal-Activated Persulfate Salts
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Inorganic persulfate salts were identified as efficient reagents for the oxidative aromatization of 3,4-dihydroquinolin-2(1H)-ones through the activation of readily available transition metals, such as iron and copper. The feasible protocol conforming to the requirement of green chemistry was utilized in the preparation of the key intermediate (7-(4-chlorobutoxy)quinolin-2(1H)-one 2) of brexpiprazole in 80% isolated yield on a 100 g scale, and different quinolin-2(1H)-one derivatives with various functional groups were demonstrated in 52-89% yields.
- Chen, Weiming,Sun, Changliang,Zhang, Yan,Hu, Tianwen,Zhu, Fuqiang,Jiang, Xiangrui,Abame, Melkamu Alemu,Yang, Feipu,Suo, Jin,Shi, Jing,Shen, Jingshan,Aisa, Haji A.
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p. 8702 - 8709
(2019/07/03)
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- Structure-functional selectivity relationship studies of β-arrestin-biased dopamine D2 receptor agonists
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Functionally selective G protein-coupled receptor (GPCR) ligands, which differentially modulate canonical and noncanonical signaling, are extremely useful for elucidating key signal transduction pathways essential for both the therapeutic actions and side
- Chen, Xin,Sassano, Maria F.,Zheng, Lianyou,Setola, Vincent,Chen, Meng,Bai, Xu,Frye, Stephen V.,Wetsel, William C.,Roth, Bryan L.,Jin, Jian
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p. 7141 - 7153
(2012/11/07)
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- PROCESS FOR SYNTHESIZING OXIDIZED LACTAM COMPOUNDS
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The invention provides a method for the synthesis of dehydrogenated lactam drugs of Formula I:
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Page/Page column 60-61
(2011/11/13)
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- 3,4-DIHYDRO-2 (1H) - QUINOLINONE AND 2 (1H)-QUINOLINONE DERIVATIVES
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The present invention relates to novel 3,4-dihydro-2(lH)-quinolinone and 2(lH)-quinolinone derivatives, their acceptable acid addition salts, solvates, hydrates and polymorphs thereof. The invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions beneficially treated by atypical antipsychotic agents. The invention further provides methods for using a compound of this invention to determine concentrations of a corresponding 3,4-dihydro-2(lH)- quinolinone or 2(lH)-quinolinone compound, particularly in biological fluids, and to determine metabolism patterns of that 3,4-dihydro-2(lH)-quinolinone or 2(1H)-quinolinone compound.
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Page/Page column 42-43
(2008/06/13)
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- Synthesis and characterization of N-oxides and metabolites of anti-psychotic drug, Aripiprazole
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Aripiprazole is a recently developed anti-psychotic drug used for the treatment of schizophrenia. Aripiprazole and its N-oxides exhibit a strong activity for influencing the neurotransmission of dopamine receptors and are devoid of side effects induced by the known drugs useful for the treatment of schizophrenia. Further, Aripiprazole is metabolized by different biotransformation pathways as dehydrogenation, hydroxylation and N-dealkylation giving rise to different metabolites. The present work details the development of a simple and novel process for the preparation of Aripiprazole N-oxides as Aripiprazole-4-N-oxide, Aripiprazole-1-N-oxide and Aripiprazole-1,4-di-N-oxide and Aripiprazole metabolites such as dehydro Aripiprazole and Aripiprazole hydroxy metabolite.
- Satyanarayana, Bollikonda,Sumalatha, Yasareni,Kumar, Sythana Suresh,Venkatraman, Sundaram,Reddy, Ghanta Mahesh,Reddy, Padi Pratap
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p. 485 - 490
(2007/10/03)
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- Novel antipsychotic agents with dopamine autoreceptor agonist properties: Synthesis and pharmacology of 7-[4-(4-phenyl-1- piperazinyl)butoxy]-3,4-dihydro-2(1H)-quinolinone derivatives
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To develop a novel antipsychotic agent which is an agonist of dopamine (DA) autoreceptors and an antagonist of postsynaptic DA receptors, a series of 7-[4-[4-(substituted phenyl)-1-piperazinyl]butoxy]-3,4-dihydro-2(1H)- quinolinones was synthesized and their dual activities were examined. The postsynaptic DA receptor antagonistic activities of the compounds were evaluated by their ability to inhibit stereotypy induced by apomorphine in mice, and the autoreceptor agonist activities were determined by their effects on the γ-butyrolactone (GBL)-induced increase in L- dihydroxyphenylalanine (DOPA) synthesis in the mouse brain. Many compounds inhibited the stereotypic behavior, and several compounds reversed the GBL- induced increase in the DOPA synthesis. Among them, 7-[4-[4-(2,3- dichlorophenyl)-l-piperazinyl]butoxy]-3,4-dihydro-2(1H)-quinolinone (28, aripiprazole, OPC-14597) was found to have these two activities. This compound reversed the GBL-induced DOPA synthesis (ED50 values of 5.1 μmol/kg po) and inhibited the APO induced stereotypy (ED50 values of 0.6 μmol/kg po). Compound 28 induced catalepsy at 10 times higher dose than that required for the antagonism of APO-induced stereotypy (ED50 value of 7.8 μmol/kg po).
- Oshiro, Yasuo,Sato, Seiji,Kurahashi, Nobuyuki,Tanaka, Tatsuyoshi,Kikuchi, Tetsuro,Tottori, Katsura,Uwahodo, Yasufumi,Nishi, Takao
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p. 658 - 667
(2007/10/03)
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