CAS No.147526-32-7,Pitavastatin calcium Suppliers

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Basic Information

Molecular Structure:
CAS No.:	147526-32-7
Name:	Pitavastatin calcium
Article Data:	38

Formula:	(C₂₅H₂₃FNO₄)₂^.Ca
Molecular Weight:	880.999
Synonyms:	Bis((3R,5S,6E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoate), monocalcium salt;6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, calcium salt (2:1), (S-(R,S-(E)))-;Pitavastatin hemicalcium;UNII-IYD54XEG3W;Livalo;CCRIS 8652;
EINECS:	807-641-2
Boiling Point:	692 °C at 760 mmHg
Flash Point:	372.3 °C
Appearance:	white to off-white powder
Safety:	24/25
PSA:	186.96000
LogP:	6.36680

Synthetic route

: 849811-78-5
methyl (3R,5S,6E)-7-{2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl}-3,5-dihydroxyhept-6-enoate

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 0.5h;	100%
With water; sodium hydroxide In methanol at 20℃; for 2h; Product distribution / selectivity;

: 147526-32-7
pitavastatin calcium salt

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
With hydrogenchloride In water; ethyl acetate at 25 - 35℃;	95.9%
With hydrogenchloride In dichloromethane; water at 0 - 25℃; for 0.833333h; pH=3;
With hydrogenchloride In water; ethyl acetate pH=4;	3.7 g
With hydrogenchloride In dichloromethane; water

: 147489-06-3
(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
Stage #1: (4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester With trifluoroacetic acid In acetonitrile at 30 - 35℃; Stage #2: With caesium carbonate In acetonitrile at 35 - 40℃;	94%
Multi-step reaction with 3 steps 1.1: water; oxalic acid / methanol / 6 h / 35 °C 1.2: 2.75 h / 10 - 30 °C / pH 7 2.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C 2.2: 0.67 h / 25 °C 3.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 4 steps 1.1: water; oxalic acid / methanol / 6 h / 35 °C 1.2: 2.75 h / 10 - 30 °C / pH 7 2.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C 2.2: 0.25 h / 0 °C / pH 4 2.3: 0.5 h / 0 °C 3.1: sodium hydroxide / water / 0.75 h / 30 °C 3.2: 0.75 h / 35 °C 4.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / acetonitrile; water / 2 h / 13 °C 2: sodium hydroxide / water / 2 h / 10 °C / Large scale View Scheme

: 167073-19-0
(E)-(3R,5S)-7-[2-cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ethyl ester

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
With ethanol; sodium hydroxide In water at 20℃; for 3h;	87.4%

: 586966-54-3
(3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
With sodium hydroxide In water at 10℃; for 2h; Large scale;	83.9%
Stage #1: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-3,5-dihydroxy-6-heptenoic acid tert-butyl ester With hydrogenchloride; water In methanol at 25℃; for 2.16667h; Stage #2: With hydrogenchloride In dichloromethane at 0 - 25℃; for 0.916667h; pH=3;
Multi-step reaction with 2 steps 1.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C 1.2: 0.67 h / 25 °C 2.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C 1.2: 0.25 h / 0 °C / pH 4 1.3: 0.5 h / 0 °C 2.1: sodium hydroxide / water / 0.75 h / 30 °C 2.2: 0.75 h / 35 °C 3.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme

: (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3R,5S,6E)-7-<2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl>-3,5-dihydroxy-6-heptenoate

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
With sodium hydroxide In methanol for 12h; Ambient temperature;

: (±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
Stage #1: (±)-E-3,5-dihydroxy-7-[2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]-6-heptenoic acid ethyl ester With sodium hydroxide Hydrolysis; Stage #2: With (+)-1-phenylethylamine resolution;

: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-[(1S)-1-phenylethyl]hept-6-enamide

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
Stage #1: (3R,5S,6E)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-[(1S)-1-phenylethyl]hept-6-enamide With sodium hydroxide In ethanol at 50 - 55℃; for 26h; Stage #2: With hydrogenchloride In ethyl acetate Further stages.;

: 121660-11-5
2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: DMSO; P2O5; Et3N 2.1: NaOH; (n-octyl)3MeNCl / toluene; H2O 3.1: DIBAH 4.1: NaH; n-BuLi 5.1: NaBH4; Et2BOMe / -78 °C 6.1: aq. NaOH 6.2: (+)-α-methylbenzylamine View Scheme
Multi-step reaction with 4 steps 1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C 1.2: 1 h / 75 °C 2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 3.1: water; oxalic acid / methanol / 6 h / 35 °C 3.2: 2.75 h / 10 - 30 °C / pH 7 4.1: hydrogenchloride; water / methanol / 2.17 h / 25 °C 4.2: 0.92 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 5 steps 1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C 1.2: 1 h / 75 °C 2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 3.1: water; oxalic acid / methanol / 6 h / 35 °C 3.2: 2.75 h / 10 - 30 °C / pH 7 4.1: sodium hydroxide; water / methanol / 1.67 h / 0 °C 4.2: 0.67 h / 25 °C 5.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 6 steps 1.1: phosphorus tribromide / dichloromethane / 1.5 h / 25 °C 1.2: 1 h / 75 °C 2.1: potassium carbonate / dimethyl sulfoxide / 7 h / 75 °C 3.1: water; oxalic acid / methanol / 6 h / 35 °C 3.2: 2.75 h / 10 - 30 °C / pH 7 4.1: sodium hydroxide; water / acetonitrile / 1.5 h / 30 °C 4.2: 0.25 h / 0 °C / pH 4 4.3: 0.5 h / 0 °C 5.1: sodium hydroxide / water / 0.75 h / 30 °C 5.2: 0.75 h / 35 °C 6.1: hydrogenchloride / dichloromethane; water / 0.83 h / 0 - 25 °C / pH 3 View Scheme
Multi-step reaction with 5 steps 1: thionyl chloride / toluene; dichloromethane / 15 °C 2: toluene / 12 h / Reflux; Large scale 3: potassium carbonate / dimethyl sulfoxide / 3 h / 30 - 50 °C / Large scale 4: hydrogenchloride / acetonitrile; water / 2 h / 13 °C 5: sodium hydroxide / water / 2 h / 10 °C / Large scale View Scheme

: 121660-37-5
2-cyclopropyl-4-(4-fluorophenyl)-3-formylquinoline

: 147526-32-7
pitavastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: NaOH; (n-octyl)3MeNCl / toluene; H2O 2.1: DIBAH 3.1: NaH; n-BuLi 4.1: NaBH4; Et2BOMe / -78 °C 5.1: aq. NaOH 5.2: (+)-α-methylbenzylamine View Scheme
Multi-step reaction with 3 steps 1.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one; 2-methyltetrahydrofuran; tetrahydrofuran / -60 - 22 °C 2.1: hydrogenchloride / acetonitrile; water / 1.5 h / 45 °C 2.2: 1.5 h 3.1: hydrogenchloride / water; ethyl acetate / pH 4 View Scheme
Multi-step reaction with 4 steps 1.1: sodium t-butanolate / 1-methyl-pyrrolidin-2-one; 2-methyltetrahydrofuran; tetrahydrofuran / -60 - 22 °C 2.1: hydrogenchloride / acetonitrile; water / 2.5 h / 45 °C 2.2: 1.5 h / 10 °C 3.1: sodium hydroxide / water / pH 12.3 3.2: 1.25 h / pH 9.7 4.1: hydrogenchloride / water; ethyl acetate / pH 4 View Scheme

Raw Materials

765-43-5

Downstream Products

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Chemistry

Molecular structure of Pitavastatin calcium (CAS NO.147526-32-7) is:

Product Name: Pitavastatin calcium
CAS Registry Number: 147526-32-7
IUPAC Name: calcium(E,3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxyhept-6-enoate
Molecular Weight: 880.983646 [g/mol]
Molecular Formula: (C₂₅H₂₃FNO₄)₂^.Ca
H-Bond Donor: 4
H-Bond Acceptor: 12
Flash Point: 372.3 °C
Enthalpy of Vaporization: 106.48 kJ/mol
Boiling Point: 692 °C at 760 mmHg
Vapour Pressure: 4.21E-20 mmHg at 25°C
Product Categories: Active Pharmaceutical Ingredients;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;chemical

Uses

Pitavastatin calcium (CAS NO.147526-32-7) can be used as a competitive inhibitor of HMG-CoA reductase.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	oral	100mg/kg (100mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA GASTROINTESTINAL: NAUSEA OR VOMITING	Oyo Yakuri. Pharmacometrics. Vol. 56, Pg. 67, 1998.
rat	LDLo	oral	500mg/kg (500mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Oyo Yakuri. Pharmacometrics. Vol. 56, Pg. 67, 1998.

Specification

Pitavastatin calcium , its cas register number is 147526-32-7. It also can be called Bis((3R,5S,6E)-7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolyl)-3,5-dihydroxy-6-heptenoate), monocalcium salt ; NK 104 ; CCRIS 8652 ; Livalo ; Pitavastatin hemicalcium ; UNII-IYD54XEG3W ; 6-Heptenoic acid, 7-(2-cyclopropyl-4-(4-fluorophenyl)-3-quinolinyl)-3,5-dihydroxy-, calcium salt (2:1), (S-(R*,S*-(E)))- .It is a white to off-white powder.