147221-93-0 Usage
Uses
Used in Pharmaceutical Industry:
Delavirdine Mesylate is used as an antiretroviral agent for the treatment of HIV-1 infection. It is specifically used in combination therapy with other antiretrovirals to enhance the effectiveness of the treatment and reduce the emergence of viral resistance. The combination therapy helps in managing the HIV infection more effectively and prolonging the time it takes for the virus to develop resistance to the drugs.
Originator
Pharmacia ＆ Upjohn (US)
Manufacturing Process
5-Nitroindole-2-carboxylic acid (0.86 g), 1-[3-(N-isopropyl)amino-2-
pyridinyl]piperazine (0.43 g), 1-(ethyl)-3-(dimethylaminopropyl)carbodiimide
(0.45 g) and THF (4 ml), were stirred at 20-25°C for 3 hr; then the reaction
mixture was dissolved in chloroform (50 ml) and extracted with saturated
aqueous sodium bicarbonate, saline, dried over anhydrous sodium sulfate and
concentrated under reduced pressure. Purification by flash column
chromatography (200 g silica) eluting with ethyl acetate/hexane (50/50), the
appropriate fractions were pooled and concentrated to give 1-[5-nitroindolyl2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine, mp 153°-
154°C.1-[5-Nitroindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-
pyridinyl]piperazine (1.0 g) was dissolved in ethanol (60 ml) and THF (60 ml)
and palladium on carbon (10%, 0.15 g) was added. The reaction mixture was
hydrogenated at 40 psi for 14 hr, then filtered through celite and concentrated
under reduced pressure. Purification by flash chromatography, eluting with
ethyl acetate/hexane (50/50) pooling and concentrating the appropriate
fractions gave 1-[5-aminoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-
pyridinyl]piperazine, mp 212°-214°C.1-[5-Aminoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-
pyridinyl]piperazine (0.075 mg) was dissolved in methylene chloride (0.4 ml)
and pyridine (0.016 g) was added and the reaction is cooled to 0°C. Then
methanesulfonyl chloride (0.023 g) was added. After 2.5 hr of stirring, the
reaction was diluted with chloroform and washed with saturated aqueous
sodium bicarbonate, saline, dried over anhydrous sodium sulfate and
concentrated under reduced pressure. The concentrate was dissolved in the
minimum amount of chloroform and passed through a small plug of silica gel
and then it is recrystallized with ethyl acetate/hexane to provide the 1-[5-
methansulfoneamidolyl-2-carbonyl]-4-[3-(1-methylethylenamino)-2-
pyridinyl]piperazine, mp 226°-228°C.
The mesylate salt may be formed by dissolving the free base in methanol and
methanesulfonic acid (1 eq) is added.
Therapeutic Function
Antiviral, Anti-HIV virus agent
Check Digit Verification of cas no
The CAS Registry Mumber 147221-93-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,7,2,2 and 1 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 147221-93:
(8*1)+(7*4)+(6*7)+(5*2)+(4*2)+(3*1)+(2*9)+(1*3)=120
120 % 10 = 0
So 147221-93-0 is a valid CAS Registry Number.
InChI:InChI=1/C22H28N6O3S.CH4O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20;1-5(2,3)4/h4-8,13-15,24-26H,9-12H2,1-3H3;1H3,(H,2,3,4)
