Tropifexor CAS#: 1383816-29-2 • ChemWhat中文网

Tropifexor CAS#: 1383816-29-2; 凯望编码 (ChemWhat Code): 1097529

Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

Identification

Structure of Tropifexor CAS 1383816-29-2

Patent Information
Patent ID	Title	Publication Date
WO2012/87519	COMPOSITIONS AND METHODS FOR MODULATING FXR	2012

Physical Data

Appearance	Powder
Solubility	No data available
Flash Point	No data available
Refractive index	No data available
Sensitivity	No data available

Melting Point, °C	Solvent (Melting Point)
221	acetonitrile

Density, g·cm^-3	Reference Temperature, °C	Measurement Temperature, °C
-173.16	4	25

Spectra

Description (NMR Spectroscopy)	Nucleus (NMR Spectroscopy)	Solvents (NMR Spectroscopy)	Frequency (NMR Spectroscopy), MHz
Chemical shifts	1H	dimethylsulfoxide-d6	400
Chemical shifts	1H	chloroform-d1	400
Chemical shifts	13C	dimethylsulfoxide-d6	100
Chemical shifts	19F	dimethylsulfoxide-d6	376
	1H	deuteromethanol	400

Description (IR Spectroscopy)	Solvent (IR Spectroscopy)	Temperature (IR Spectroscopy), °C
Bands	potassium bromide	27
Spectrum	CCl4	14.85 – 54.85

Description (UV/VIS Spectroscopy)

Bands

Description (Mass Spectrometry)

high resolution mass spectrometry (HRMS), time-of-flight mass spectra (TOFMS), electrospray ionisation (ESI), liquid chromatography mass spectrometry (LCMS), spectrum

liquid chromatography mass spectrometry (LCMS), electrospray ionisation (ESI), spectrum

Route of Synthesis (ROS)

Conditions

Yield

With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;

Experimental Procedure
6.1 first step2-((2-((1R, 3R, 5S) -3-((5-cyclopropyl-3- (2- (trifluoromethoxy) phenyl) isoxazol-4-yl) methoxy ) -8-azabicyclo [3.2.1] oct-8-yl) -4-fluorobenzo [d] thiazole-6-formylamino) oxy) ethyl acetate
Under the protection of argon, 2-((1R, 3R, 5S) -3-((5-cyclopropyl-3- (2- (trifluoromethoxy) phenyl) isoxazol-4-yl) (Methoxy) -8-azabicyclo [3.2.1] oct-8-yl) -4-fluorobenzo [d] thiazole-6-carboxylic acid 5a (180 mg, 0.3 mmol, according to published patent application “WO 2012087519 “, 2- (aminooxy) ethyl acetate 6a (53.6 mg, 0.45 mmol, prepared according to published patent application” WO 2002103008 “), 2- (7-azobenzotriazole) -N, N, N ‘, N’-Tetramethylurea hexafluorophosphate (HATU) (171 mg, 0.45 mmol) and triethylamine (60.6 mg, 0.2 mmol) were dissolved in 10 mL of N, N-dimethylformamide At room temperature, the reaction was allowed to proceed overnight. 100 mL of water was added, extraction was performed with ethyl acetate (100 mL), and the organic phase was washed with a saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was subjected to thin layer chromatography (developed Agent: System A) was purified to obtain 2-((2-((1R, 3R, 5S) -3-((5-cyclopropyl-3- (2- (trifluoromethoxy) phenyl) isoxamine Azole-4-yl) methoxy) -8-azabicyclo [3.2.1] oct-8-yl) -4-fluorobenzo [d] thiazole-6-formylamino) oxy) ethyl acetate 6b (140 mg, yellow oil)

66%

Safety and Hazards

GHS Hazard Statements

Not Classified

Other Data

Transportation	Under the room temperature and away from light
HS Code	No data available
Storage	Under the room temperature and away from light
Shelf Life	1 year
Market Price	USD

Druglikeness
Lipinski rules component
分子量	603.594
logP	6.823
HBA	5
HBD	1
Matching Lipinski Rules	2
Veber rules component
Polar Surface Area (PSA)	126.16
Rotatable Bond (RotB)	9
Matching Veber Rules	2

Bioactivity

In vitro: Efficacy

Quantitative Results

pX	Parameter	Value (qual)	Value (quant)	Unit	Dose
10	mRNA expression level increase(of mRNA level)	Active			0.0001 μM
9.72	EC50		0.00019	µM
9.7	EC50		0.2	nM
9.59	EC50		0.26	nM
9	mRNA expression level increase(of mRNA level)	Active			0.001 -1 μM
1	EC50	>	10	µM
1	EC50	>	10	µM
	mRNA expression level increase(of mRNA level)		3	fold	1 nM
	mRNA expression level increase(of mRNA level)	>	15	fold	10nM

In vivo: Animal Model

Quantitative Results

pX	Parameter	Value (quant)	Biological Species	Route of administration	Dose
9.92	concentration (parameter)	0.12	rat	oral administration	0.003mg/kg
9.7	concentration (parameter)	0.2	rat	oral administration	0.003mg/kg
9.51	concentration (parameter)	0.31	rat	oral administration	0.01mg/kg
9.43	concentration (parameter)	0.37	rat	oral administration	0.01mg/kg
8.89	concentration (parameter)	1.16	rat	oral administration	0.03mg/kg
8.64	concentration (parameter)	1.29	rat	oral administration	0.03mg/kg
7.79	concentration (parameter)	16.41	rat	oral administration	1 mg/kg
7.2	concentration (parameter)	62.61	rat	oral administration	3 mg/kg

Metabolism

Quantitative Results

Parameter	Value (qual)	Value (quant)	Unit
extraction ratio		0.55	no unit
extraction ratio	<	0.18	no unit

Pharmacokinetic

Quantitative Results

Parameter	Value (quant)	Biological Species	Route of administration	Dose
CL (drug clearance)	5.3	mouse	intravenous administration	5 mg/kg
Vdss	0.7	mouse	intravenous administration	5 mg/kg
half life time	2.6	mouse	intravenous administration	5 mg/kg
AUC	4785	mouse	oral administration	10 mg/kg
Cmax	1186	mouse	oral administration	10 mg/kg
plasma protein-bound fraction	99	dog	oral administration	2 mg/kg
AUC (0-24 h)	117	rat	oral administration	0.3 mg/kg
F (drug bioavailability)	10	rat	oral administration	1 mg/kg

Use Pattern

Tropifexor CAS#: 1383816-29-2 as Pharmaceuticals

reducing at least one point in severity of nonalcoholic fatty liver disease grading scoring systems in combination with (S)-2-(5-((3-ethoxypyridin-2-yl)oxy)pyridin-3-yl)-N-(tetrahydrothran-3-yl)pyrimidine-5-carboxamide and 4-(4-(1-isopropyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4’-piperidine]-1’-carbonyl)-6-methoxypyridin-2-yl)benzoic acid

reducing at least one point in severity of nonalcoholic steatohepatitis grading scoring systems

FXR mediated disorder or condition

alcohol-induced cirrhosis

cholestasis of pregnancy

cystic fibrosis or liver fibrosis

Tropifexor CAS#: 1383816-29-2 used as for liver cirrhosis


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认证生产商
Caming Pharmaceutical Ltd	http://www.caming.com/
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Watson International Limited	访问Watson官网


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英文名	Tropifexor
IUPAC Name	2-[(1R,5S)-3-[[5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl]methoxy]-8-azabicyclo[3.2.1]octan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid
分子结构
CAS编号	1383816-29-2
EINECS Number	No data available
MDL Number	MFCD31693060
Beilstein Registry Number	No data available
别名	2-[(1R,3r,5S)-3-({5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]-1,2-oxazol-4-yl}methoxy)-8-azabicyclo[3.2.1]octan-8-yl]-4-fluoro-1,3-benzothiazole-6-carboxylic acid, 2-[3-({5-cyclopropyl-3-[2-(trifluoromethoxy)phenyl]1,2-oxazol-4-yl}methoxy)-8-azabicyclo[3.2.1]octan-8-yl]4-fluoro-1,3-benzothiazole-6-carboxylic acid, 2-(3-((5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-4-fluorobenzo[d]thiazole-6-carboxylic acid, tropifexor, LJN452
分子式	C₂₉H₂₅F₄N₃O₅S
分子量	603.584
InChI	InChI=1S/C29H25F4N3O5S/c30-21-9-15(27(37)38)10-23-25(21)34-28(42-23)36-16-7-8-17(36)12-18(11-16)39-13-20-24(35-41-26(20)14-5-6-14)19-3-1-2-4-22(19)40-29(31,32)33/h1-4,9-10,14,16-18H,5-8,11-13H2,(H,37,38)/t16-,17+,18+
InChI Key	VYLOOGHLKSNNEK-PIIMJCKOSA-N
Canonical SMILES	c1ccc(c(c1)c2c(c(on2)C3CC3)CO[C@H]4C[C@H]5CC[C@@H](C4)N5c6nc7c(cc(cc7s6)C(=O)O)F)OC(F)(F)F

Identification

Physical Data

Spectra

Route of Synthesis (ROS)

Safety and Hazards

Other Data

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