RILPIVIRINE HCL
- CAS No.
- 700361-47-3
- Chemical Name:
- RILPIVIRINE HCL
- Synonyms
- Rilpivirine Hydrochloride;RILPIVIRINE HCL;Rilpivirine-d6 HCl;Rilpivirine HCl (TMC278;Ripivirine Hydrochloride;TMC 278. trade name Edurant
- CBNumber:
- CB62455679
- Molecular Formula:
- C22H19ClN6
- Molecular Weight:
- 402.89
- MDL Number:
- MFCD11046523
- MOL File:
- 700361-47-3.mol
- MSDS File:
- SDS
| storage temp. | Store at -20°C |
|---|---|
| solubility | DMSO:50.0(Max Conc. mg/mL);136.46(Max Conc. mM) |
| FDA UNII | 212WAX8KDD |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H302-H319 |
| Precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P305+P351+P338-P337+P313P |
RILPIVIRINE HCL Chemical Properties,Uses,Production
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.
RILPIVIRINE HCL Preparation Products And Raw materials
Raw materials
Preparation Products
RILPIVIRINE HCL Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| SHANGHAI T&W PHARMACEUTICAL CO., LTD. | +86-021-61551413 +8618813727289 | contact@trustwe.com | China | 5738 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354 +1-00000000000 | marketing@targetmol.com | United States | 19892 | 58 |
| Alfa Chemistry | +1-5166625404 | Info@alfa-chemistry.com | United States | 21317 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
| Nantong HI-FUTURE Biology Co., Ltd. | +undefined18051384581 | sales@chemhifuture.com | China | 3136 | 58 |
| Shenzhen Monkono Technology Co.,Ltd | +86-17063441314 | sansbiotech@outlook.com | China | 677 | 58 |
| LEAPCHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 43348 | 58 |
| CONTIDE BIOTECH CO.,LTD | +85253358525 | xena@healthtide-api.com | China | 499 | 58 |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131981 | 58 |