1083076-69-0 Usage
Uses
Used in Pharmaceutical Industry:
RGH188 hydrochloride is used as an atypical antipsychotic for the treatment of schizophrenia and bipolar I disorder. Its unique mechanism of action, involving partial agonism at dopamine D2/D3 and serotonin 5-HT1A receptors, as well as antagonism at serotonin 5-HT2A receptors, contributes to its effectiveness in managing the symptoms of these conditions.
Used in Clinical Trials:
RGH188 hydrochloride is used as a test compound in clinical trials to evaluate its efficacy in improving the symptoms of schizophrenia and bipolar mania. In these trials, the drug has demonstrated significant improvement compared to placebo as measured by the Young Mania Rating Scale (YMRS) total scores in patients with bipolar mania and by the Positive and Negative Syndrome Scale (PANSS) total scores in patients with schizophrenia.
Used in Drug Metabolism Studies:
RGH188 hydrochloride is used as a subject of study in drug metabolism research, focusing on its extensive metabolism by CYP3A4 and, to a lesser extent, CYP2D6. Understanding the metabolic pathways of the drug can help optimize its dosing regimens and minimize potential drug-drug interactions.
Used in Drug Delivery Systems:
RGH188 hydrochloride can be used as an active pharmaceutical ingredient in the development of novel drug delivery systems, such as extended-release formulations or targeted drug delivery systems, to improve patient compliance and therapeutic outcomes.
Used in Intellectual Property and Licensing:
RGH188 hydrochloride is used as a basis for intellectual property and licensing agreements between pharmaceutical companies. Forest Laboratories (now Allergan) has exclusive rights to cariprazine in the U.S. and Canada, while Mitsubishi Pharma Corporation has exclusive rights to the sale of the drug in Japan and Asia. These agreements facilitate the distribution and commercialization of the drug in different markets.
Synthesis
While the synthesis of cariprazine hydrochloride has been
reported in a number of patents as well as its discovery
synthesis in the publicly disclosed literature, the process route
has not yet been disseminated. Starting with the reduction of commercial 2-(4-
nitrophenyl)acetic acid (69) via hydrogenation in water in
the presence of Pd/C, this reaction proceeds a one-pot,
stepwise reduction of the nitro group. A separate reduction
event converting the phenyl ring to the corresponding
cyclohexane provides 4-aminocyclohexylacetic acid with 60-70% selectivity for the desired trans isomer. Following filtration
and distillation, the crude aqueous solution was treated with
HCl in refluxing ethanol to generate the corresponding ethyl
ester 70. Crystallization from acetonitrile gave the HCl salt in
high purity and 40% yield over two steps (a reaction sequence
that was reported on 200 kg scale). Amine 70 was transformed
into intermediate 73 via Boc protection followed by ester
reduction to the primary alcohol 71, which was obtained as a
solution in toluene following extraction. Next, mesylation of the
alcohol followed by alkylation with commercially available
piperazine 72 provided piperazinyl cyclohexane 73 in 70% over
the four-step sequence. The carbamate protecting group within
73 was removed via acidic ethanolysis, and the resulting
product was treated with triphosgene and dimethylamine to
generate cariprazine as the freebase. Salt formation by means of
methanolic HCl ultimately furnished cariprazine hydrochloride
IX in 85% yield from 73.
Check Digit Verification of cas no
The CAS Registry Mumber 1083076-69-0 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,8,3,0,7 and 6 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 1083076-69:
(9*1)+(8*0)+(7*8)+(6*3)+(5*0)+(4*7)+(3*6)+(2*6)+(1*9)=150
150 % 10 = 0
So 1083076-69-0 is a valid CAS Registry Number.
1083076-69-0Relevant articles and documents
A PROCESS FOR THE PREPARATION OF CARIPRAZINE SALT
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Page/Page column 13; 19, (2021/02/05)
A process for the preparation of cariprazine hydrochloride (Formula I) by reacting trans-4-{2-[4-(2,3-dichlorophenyl)piperazin-1-yl]ethyl}cyclohexanamine (Formula II) or it's salt with N,N-dimethylcarbamoyl chloride (Formula III) in a biphasic solvent system containing an organic solvent phase and an aqueous phase, in the presence of a base.
NOVEL PROCESS FOR THE PREPARATION OF PIPERAZINE COMPOUNDS AND HYDROCHLORIDE SALTS THEREOF
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Page/Page column 10-11, (2011/07/07)
The invention relates to a new process for the preparation of compounds of general formula (I) wherein R1 and R2 represent independently hydrogen or C1-6 alkyl with straight or branched chain optionally substituted with ar
NOVEL SALTS OF PIPERAZINE COMPOUNDS AS D3/D2 ANTAGONISTS
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Page/Page column 7, (2009/02/11)
The present invention relates to novel monohydrochloride, dihydrochloride, monohydrobromide, maleate and methanesulphonate salts of trans 4-{2-[4-(2,3-dichlorophenyl)-piperazine-1-yl]-ethyl}-N,N-dimethylcarbamoyl-cyclohexylamine and/or their hydrates and/
