700361-47-3 Usage
Uses
Rilpivirine Hydrochloride was shown to be able to treat and or prevent immunodeficiency virus-1. It also has uses for anti-viral therapy
Definition
ChEBI: A hydrochloride obtained by reaction of rilpivirine with one equivalent of hydrochloric acid. Used for treatment of HIV.
Clinical Use
Rilpivirine hydrochloride (Edurant), a non-nucleoside reverse
transcriptase inhibitor (NNRTI), received its approval both from
the U.S. FDA and E.U. EMA in 2011 for the treatment of HIV-1 infection in treatment-na?ve adult patients. It was discovered and
developed by Janssen Pharmaceuticals and its subsidiary Tibotec
Pharmaceuticals. As a second generation NNRTI, rilpivirine hydrochloride
displayed higher potency and longer half-life with a 25 mg
once a day dose, compared to existing NNRTIs, such as the 200 mg
BID of efavirenze (Sustiva). In late 2011, the fixed-dose
combination products of rilpivirine hydrochloride with two
nucleoside reverse transcriptase inhibitor (RTIs) emtricitabine and tenofovir disoproxil fumarate, co-developed by Gilead Science
and Tibotec, were also approved both by the FDA and EMA under
brand names Complera? and Eviplera?, respectively.
Synthesis
Similar
to efavirenze, rilpivirine hydrochloride is a diarylpyrimidine
(DAPY) compound, and the large-scale process synthesis begins
with commercially available 2-methylthio-4-pyrimidinone (193)
shown in the scheme.Thioether 193 was condensed with neat 4-cyanoaniline (194) at
elevated temperature to afford diarylamine 195 in 77% yield. Subsequent
treatment of pyrimidone 195 with refluxing POCl3 provided
the corresponding chloride 196 in 77% yield.160,161 In the
presence of K2CO3, chloride 196 was treated with the (E)-cinnamonitrile
aniline 200 to give rilpivirine hydrochloride (XIX) in good
yield.158 Aniline 200 was prepared via a Heck reaction of commercially
available 4-iodo-2,6-dimethyl-benzeneamine (197) and
acrylonitrile (198) affording compound 199 as a 4:1 mixture of E/Z isomers. The distribution of E/Z olefins was increased to 98:2
by salt formation and recrystallization to ultimately provide pure
(E)-200 in 64% yield for two steps.
Check Digit Verification of cas no
The CAS Registry Mumber 700361-47-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 7,0,0,3,6 and 1 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 700361-47:
(8*7)+(7*0)+(6*0)+(5*3)+(4*6)+(3*1)+(2*4)+(1*7)=113
113 % 10 = 3
So 700361-47-3 is a valid CAS Registry Number.
700361-47-3Relevant articles and documents
Method for preparing high-purity ribavirin intermediate by one-pot method (by machine translation)
-
, (2020/12/14)
The invention relates to the technical field of chemical medicine, in particular to a method for preparing a high-purity ribavirin intermediate by a one-pot method. The method comprises the following steps: (1) replacing the compound I with the compound II to obtain the reaction liquid of the compound III. (2) Acrylamide was added to III reaction liquid of the compound, and the reaction liquid of compound IV was obtained under Heck reaction conditions. (3) In the reaction solution of Compound IV, activated carbon is first added for decolorization treatment, and then a poor solvent is added for crystallization to obtain a white compound IV, i.e. a ripe intermediate. The method for preparing the high-purity ribavirin intermediate by one-pot method is scientific, reasonable, simple and feasible, improves product purity and yield, and is suitable for large-scale production. (by machine translation)
RILPIVIRINE PROCESS
-
, (2014/09/30)
Disclosed is process for the preparation of a key Rilpivirine intermediate namely, (E)-4-(2-cyanoethenyl)-2,6-dimethylphenylamine hydrochloride (II) by a process comprising reaction of the tetrafluoroborate salt of the diazonium ion of 2,6-dimethyl-4-amin
