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1009119-64-5

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  • High Quality 99% Dimethyl (2S, 2'S)-1, 1'-((2S, 2'S)-2, 2'-(4, 4'-(biphenyl-4, 4'-diyl)bis(1H-imidazole-4, 2-diyl))bis(pyrrolidine-2, 1-diyl))bis(3-methyl-1-oxobutane-2, 1-diyl)dicarbamate 1009119-64-

    Cas No: 1009119-64-5

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1009119-64-5 Usage

Anti-hepatitis C virus drugs

Daclatasvir (Daklinza) has obtained "priority review" status, combined with sorafenib for the treatment of genotype III adult patients with chronic hepatitis C. Daklinza has been the first drug that has been proved of being effective in the treatment of genotype III hepatitis C virus infection without the co-administration with interferon or ribavirin. Interferon and ribavirin are two drugs approved by FDA for the treatment of hepatitis C virus infection. Hepatitis C is a viral disease that can cause inflammation of the liver, resulting in decreased liver function or liver failure. Most patients infected with hepatitis C have no symptoms until liver damage becomes apparent, which may take several years. Globally, genotype III hepatitis C is the second most common genotype of hepatitis C after genotype 1 hepatitis C and is considered to be one of the most refractory genotype diseases. Daklinza is a pan-genotype NS5A replication complex inhibitor, with efficacy of inhibition of RNA replication and viral assembly, dual antiviral effect. For in vitro studies, Daklinza has been demonstrated to have anti-viral effect against genotype 1~6 hepatitis C virus. Daklinza is accompanied by a warning that the combination of amiodarone, Daklinza and Sofosbuvir may cause severe reduced heart rate. Daklinza is an oral tablet with the recommended dose of 60 mg for 1 times/d, in conjunction with Sofosbuvir for a total of 12 weeks. 【Research and development company】 Bristol-Myers Squibb. 【Patent Literature】 WO 2008021927A2 (August 9, 2007). 【Time of marketing】 July 24, 2015 listed in the United States, trade name Daklinza. 【Indications】 Used in combination with Sofosbuvir for the treatment of genotype 3 chronic hepatitis C (HCV) infection. 【Mechanism of action】 HCV nonstructural protein 5A (NS5A) inhibitors. Adverse reactions: headaches and fatigue. 【Formulation and specifications】 Tablets, 30 and 60mg. ? Figure 1 the structure of Daklinza The above information is edited by the Dongfang of lookchem. (2016-03-03)

Market status

Daklinza is an inhibitor of hepatitis C virus (HCV) NS5A that is useful in the treatment of genotype 3 chronic hepatitis C infection. On July 24, 2015, the FDA approved the chronic hepatitis C drug (Bristol-Myers Squibb) for marketing. The FDA approval process of Daklinza (Bristol-Myers Squibb) has undergone twists and turns. It has been once rejected by the FDA, but finally approved in mid – 2015. The FDA approved the combination of Daklinza and Sofosbuvir for the treatment of hepatitis C gene type 3 patients. In fact, as early as before the FDA approval, Daklinza had been approved for marketing in Japan, the European Union and South Korea and other countries. In 2014, Japanese health sector approved the application of Daklinza and asunaprevir (Sunvepra) for the treatment of genotype 1 infection. The European Union also approved Daclatasvir to be used in combination with other drugs in the treatment of HCV genotypes 1, 2, 3 and 4 in 2014. Daclatasvir is the first NS5A complex inhibitor approved by European Union (EU). When used in combination with other drugs, compared with the treatment combination of interferon and ribavirin which takes 48 weeks, it has a shorter duration of treatment (12 weeks or 24 weeks). Daclathavir monotherapy is not recommended, the current mainstream protocol is combination therapy of dacastavir+ sofosbuvir, which is characterized by good efficacy, higher SVR, small side effects and further shortened treatment cycle than other options. ? Figure 2 Daclatasvir tablets from United States Bristol-Myers Squibb Company

Biological activity

Daclatasvir (BMS-790052) is a highly selective HCV NS5A inhibitor with an EC50 of 9-50 pM. It acts on the infectious virus of various HCV replication genotypes and JFH-1 genotype 2a in cell cultures. Phase III;

In vitro study

BMS-790052 is one of the most potent HCV replication inhibitors reported so far with EC50 values of 50 and 9 pM on HCV genotype 1a and 1b replicons, respectively. BMS-790052 treatment index (CC50/EC50) is 105 or more. It has no effect on the 10 RNA and DNA viruses in group I with EC50 being greater than 10 μM. BMS-790052 is only effective in the treatment of HCV. BMS-790052 acts on the Huh7 cells containing the HCV genotype 1b replicon and BMS-790052 inhibits transient and stable HCV chromosome replication with an EC50 of 1-15 pM. BMS-790052 (100 pM or 1 nM) changes the subcellular localization and biochemical structure of NS5A. BMS-790052 can inhibit the heterozygous replicon containing HCV genotype-4 NS5A gene with an EC50 of 7-13 pM. The NS5A residue 30 in the heterozygous replicon is an important site for selection of resistance to BMS-790052.

Feature

BMS-790052 is a first-class, highly selective hepatitis C virus (HCV) NS5A inhibitor with an EC50 range at picomolar.

Uses

Daclatasvir, inhibits the HCV protein NS5A, and thus can be used as a drug candidate for the treatment of hepatitis C (HCV).

Definition

ChEBI: A member of the class of biphenyls that is a potent inhibitor of nonstructural protein 5A and is used (as its hydrochloride salt) for treatment of hepatitis C.

Clinical Use

Inhibitor of nonstructural protein 5A (NS5A):Treatment of chronic hepatitis C infection in combination with other medication

Drug interactions

Potentially hazardous interactions with other drugsAldesleukin: avoid concomitant use.Antipsychotics: avoid with clozapine, increased risk of agranulocytosis.

Metabolism

Dacarbazine (DTIC) is assumed to be inactiveDacarbazine is extensively metabolised in the liver Dacarbazine is extensively metabolised in the liver by the cytochrome P450 isoenzymes CYP1A2 and CYP2E1 (and possibly in the tissues by CYP1A1) to its active metabolite 5-(3-methyl-triazen-1-yl)- imidazole-4-carboxamide (MTIC), which spontaneously decomposes to the major metabolite 5-amino-imidazole- 4-carboxamide (AIC). About half of a dose is excreted in the urine by tubular secretion; 50% as unchanged DTIC and approximately 50% as AIC.

Check Digit Verification of cas no

The CAS Registry Mumber 1009119-64-5 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,0,0,9,1,1 and 9 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 1009119-64:
(9*1)+(8*0)+(7*0)+(6*9)+(5*1)+(4*1)+(3*9)+(2*6)+(1*4)=115
115 % 10 = 5
So 1009119-64-5 is a valid CAS Registry Number.
InChI:InChI=1S/C40H50N8O6/c1-23(2)33(45-39(51)53-5)37(49)47-19-7-9-31(47)35-41-21-29(43-35)27-15-11-25(12-16-27)26-13-17-28(18-14-26)30-22-42-36(44-30)32-10-8-20-48(32)38(50)34(24(3)4)46-40(52)54-6/h11-18,21-24,31-34H,7-10,19-20H2,1-6H3,(H,41,43)(H,42,44)(H,45,51)(H,46,52)/t31-,32-,33-,34-/m0/s1

1009119-64-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name daclatasvir

1.2 Other means of identification

Product number -
Other names Carbamic acid, N,?N'-?[[1,?1'-?biphenyl]?-?4,?4'-?diylbis[1H-?imidazole-?5,?2-?diyl-?(2S)?-?2,?1-?pyrrolidinediyl[(1S)?-?1-?(1-?methylethyl)?-?2-?oxo-?2,?1-?ethanediyl]?]?]?bis-?, C,?C'-?dimethyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1009119-64-5 SDS

1009119-64-5Synthetic route

C56H62N8O10

C56H62N8O10

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
With palladium on activated charcoal In methanol at 35 - 40℃; Inert atmosphere;95%
C54H58N8O8

C54H58N8O8

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
With sodium methylate In methanol at 0 - 25℃;94%
C50H66N8O10

C50H66N8O10

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water at 0 - 35℃;92%
(R)-2-[tert-butoxycarbonyl(methoxyformyl)amino]-3-methylbutanoic acid

(R)-2-[tert-butoxycarbonyl(methoxyformyl)amino]-3-methylbutanoic acid

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / tetrahydrofuran / 30 - 35 °C
1.2: 0.5 h / 0 - 5 °C
1.3: 20 - 25 °C
2.1: ammonium formate / diethylene glycol dimethyl ether / 100 - 105 °C
3.1: hydrogenchloride / ethanol; water / 0 - 35 °C
View Scheme
C50H66N4O16

C50H66N4O16

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate / diethylene glycol dimethyl ether / 100 - 105 °C
2: hydrogenchloride / ethanol; water / 0 - 35 °C
View Scheme
(R)-2-[benzoyl(methoxyformyl)amino]-3-methylbutanoic acid

(R)-2-[benzoyl(methoxyformyl)amino]-3-methylbutanoic acid

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 30 - 35 °C
1.2: 0.5 h / 0 - 5 °C
1.3: 20 - 25 °C
2.1: ammonium acetate / diethylene glycol dimethyl ether / 100 - 105 °C
3.1: sodium methylate / methanol / 0 - 25 °C
View Scheme
C54H58N4O14

C54H58N4O14

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium acetate / diethylene glycol dimethyl ether / 100 - 105 °C
2: sodium methylate / methanol / 0 - 25 °C
View Scheme
(R)-2-(benzyloxycarbonyl(methoxyformyl)amino)-3-methylbutanoic acid

(R)-2-(benzyloxycarbonyl(methoxyformyl)amino)-3-methylbutanoic acid

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: caesium carbonate / acetonitrile / 30 - 35 °C
1.2: 0.5 h / 0 - 5 °C
1.3: 20 - 25 °C
2.1: ammonium formate / diethylene glycol dimethyl ether / 100 - 105 °C
3.1: palladium on activated charcoal / methanol / 35 - 40 °C / Inert atmosphere
View Scheme
C56H62N4O16

C56H62N4O16

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonium formate / diethylene glycol dimethyl ether / 100 - 105 °C
2: palladium on activated charcoal / methanol / 35 - 40 °C / Inert atmosphere
View Scheme
L-proline
147-85-3

L-proline

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 30 - 35 °C
1.2: 0.5 h / 0 - 5 °C
1.3: 20 - 25 °C
2.1: ammonium acetate / diethylene glycol dimethyl ether / 100 - 105 °C
3.1: sodium methylate / methanol / 0 - 25 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium carbonate / tetrahydrofuran / 30 - 35 °C
1.2: 0.5 h / 0 - 5 °C
1.3: 20 - 25 °C
2.1: ammonium formate / diethylene glycol dimethyl ether / 100 - 105 °C
3.1: hydrogenchloride / ethanol; water / 0 - 35 °C
View Scheme
Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate
1009119-64-5

Methyl [(2S)-1-{(2S)-2-[4-(4’-{2-[(2S)-1-{(2S)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-pyrrolidinyl]-1H-imidazol-4-yl}-4-biphenylyl)-1H-imidazol-2-yl]-1-pyrrolidinyl}-3-methyl-1-oxo-2-butanyl]carbamate

C40H50N8O6

C40H50N8O6

Conditions
ConditionsYield
With cytochrome p450 3a Enzymatic reaction;

1009119-64-5Upstream product

1009119-64-5Downstream Products

1009119-64-5Relevant articles and documents

One-pot preparation technology of NS5A protein inhibitor daclatasvir

-

, (2020/03/23)

The invention discloses a one-pot preparation technology of an NS5A protein inhibitor daclatasvir. The technology mainly comprises the following three steps: 1) preparing an intermediate DT1: carryingout a butt reaction on reaction initial raw materials which are DTM1, DTM2 and DTM3 under the action of an alkali reagent and a condensing agent to prepare the intermediate DT1; 2) preparing an intermediate DT2: cyclizing the intermediate DT1 and an amine compound to prepare the intermediate DT2; and 3) preparing daclatasvir: removing an amino protecting group from the intermediate DT2 by using an amino protecting group removing reagent to prepare the product daclatasvir. The method for preparing daclatasvir has the characteristics of high product yield, simple and easy-to-operate overall process, no strong corrosive substances in the preparation materials, effectiveness in safety ensuring, and suitableness for large-scale industrial production.

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