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Chemical Structure| 61338-13-4 Chemical Structure| 61338-13-4
Chemical Structure| 61338-13-4

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CAS No.: 61338-13-4

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Product Details of [ 61338-13-4 ]

CAS No. :61338-13-4
Formula : C17H19N3O2
M.W : 297.35
SMILES Code : CN1CCN(C(C1)C1=CC=CC=C1)C1=C(C=CC=N1)C(O)=O
MDL No. :MFCD08458719
InChI Key :HCVDLMUVEGPGGH-UHFFFAOYSA-N
Pubchem ID :9839188

Safety of [ 61338-13-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Calculated chemistry of [ 61338-13-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 22
Num. arom. heavy atoms 12
Fraction Csp3 0.29
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 91.94
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

56.67 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.05
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.1
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.19
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.78
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.49
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.08

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.83
Solubility 4.44 mg/ml ; 0.0149 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.64
Solubility 68.5 mg/ml ; 0.23 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.85
Solubility 0.0425 mg/ml ; 0.000143 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-8.18 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<0.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.77

Application In Synthesis of [ 61338-13-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 61338-13-4 ]
  • Downstream synthetic route of [ 61338-13-4 ]

[ 61338-13-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 61338-13-4 ]
  • [ 61337-89-1 ]
YieldReaction ConditionsOperation in experiment
89% With lithium aluminium tetrahydride In tetrahydrofuran at 25 - 30℃; for 3.5 h; To a 2 L four-necked flask equipped with a stirring blade and a thermometer, 1618 mL (1618 mmol) of a 1 mol / L lithium aluminum hydride / tetrahydrofuran solution was added, and a solution of 120 g (404 mmol) of the pyridine carboxylic acid compound dissolved in 1800 mL of tetrahydrofuran While maintaining the temperature around 25 ° C., the mixture was added dropwise over 30 minutes and then stirred at 25 ° C. for 3 hours. 70 mL of water was added while cooling the reaction solution with water, and the mixture was stirred. Then, the organic layer and the aqueous layer were separated, and the obtained organic layer was sequentially washed with 70 mL of a 15 wtpercent sodium hydroxide aqueous solution and then with 200 mL of water, and separated, . The obtained organic layer was concentrated under reduced pressure to obtain a crude product of pyridine methanol compound.840 mL of isopropyl acetate was added to the crude product of the pyridine methanol compound and heated to 60 ° C. to dissolve the crude product and then 840 mL of heptane was added dropwise at an internal temperature of 50 ° C. or higher. The solution was cooled to 5 ° C.,The slurry of the pyridine methanol compound was aged at around 5 ° C. for 2 hours, and then the slurry solution was filtered by vacuum filtration. The filtered crystals were washed with a mixed solution of 60 mL of isopropyl acetate and 60 mL of heptane, and the resulting white crystals were dried under reduced pressure at 40 ° C. for 5 hours to obtain 102 g (363 mol, production yield: 89percent) of pyridine methanol compound as white crystals. 9percent) was obtained (purity: 99.53percent, water content: 320 ppm).
89.4% With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 10 - 40℃; for 5 h; Inert atmosphere Into a 1 L four-necked flask equipped with a stirring blade and a thermometer,480 g (1.61 mol) of 2- (4-methyl-2-phenyl-1-piperazinyl) -3-pyridinecarboxylic acid and 2160 mL of tetrahydrofuran were added and suspended, and the mixture was cooled to 10 ° C. Under nitrogen atmosphere, 1920 g (5.65 mol) of 70percent sodium dihydrobis (2-methoxyethoxy) aluminate in toluene solution was added dropwise, followed by reaction at 40 ° C. for 5 hours. After completion of the reaction, 2200 mL of water was added, the resulting precipitate was removed by filtration, and an organic layer and an aqueous layer were separated. To the organic layer was added 960 mL of 25 wtpercent saline, washed and separated, and the obtained organic layer was concentrated under reduced pressure. 1920 mL of toluene was added to the obtained residue, and the mixture was heated to 60 to 65 ° C., and insoluble matter was filtered off. After concentrating the toluene layer under reduced pressure, a crude product of pyridine methanol compound was obtained.To the crude product of pyridine methanol compound, 3360 mL of isopropyl acetate was added and heated to 60 ° C. to dissolve the crude product, then 3360 mL of heptane was added dropwise at an internal temperature of 50 ° C. or higher. The solution was cooled to 5 ° C. and the slurry of the pyridine methanol compound was aged at around 5 ° C. for about 2 hours. After aging, the slurry solution was filtered, and the obtained white crystals were dried under reduced pressure at 40 ° C. for 5 hours to obtain 408 g (1.44 mol) of pyridinemethanol compound as white crystals (production yield: 89.4percent) .
89.4% With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 40℃; for 5 h; Inert atmosphere 480 g (1.61 mol) of 2- (4-methyl-2-phenyl-1-piperazinyl) -3-pyridinecarboxylic acid and 2160 mL of tetrahydrofuran were added and suspended in a 1 L four-necked flask equipped with a stirrer and a thermometer , And cooled to 10 ° C. Under nitrogen atmosphere, 1920 g (5.65 mol) of 70percent sodium dihydrobis (2-methoxyethoxy) aluminate in toluene solution was added dropwise, followed by reaction at 40 ° C. for 5 hours. After completion of the reaction, 2200 mL of water was added, the resulting precipitate was removed by filtration, and an organic layer and an aqueous layer were separated. To the organic layer was added 960 mL of 25 wtpercent saline, washed and separated, and the obtained organic layer was concentrated under reduced pressure. 1920 mL of toluene was added to the obtained residue, and the mixture was heated to 60 to 65 ° C., and insoluble matter was filtered off. After concentrating the toluene layer under reduced pressure, a crude product of pyridine methanol compound was obtained.To the crude product of pyridine methanol compound, 3360 mL of isopropyl acetate was added and heated to 60 ° C. to dissolve the crude product, then 3360 mL of heptane was added dropwise at an internal temperature of 50 ° C. or higher. The solution was cooled to 5 ° C. and the slurry of the pyridine methanol compound was aged at around 5 ° C. for about 2 hours. After aging, the slurry solution was filtered, and the obtained white crystals were dried under reduced pressure at 40 ° C. for 5 hours to obtain 408 g (1.44 mol) of pyridinemethanol compound as white crystals (production yield: 89.4percent) .
89.9% With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 3.5 h; 1618 mL (1618 mmol) of a 1 mol / L lithium aluminum hydride / tetrahydrofuran solution was added to a 2 L four-necked flask equipped with a stirring blade and a thermometer,Pyridine carboxylic acid compound 120 g (404 mmol)In 1,800 mL of tetrahydrofuran was added dropwise over 30 minutes while maintaining the internal temperature at around 25 ° C., and the mixture was stirred at 25 ° C. for 3 hours.70 mL of water was added while cooling the reaction solution with water, and the mixture was stirred. Then, the organic layer and the aqueous layer were separated, and the obtained organic layer was sequentially washed with 70 mL of a 15 wtpercent sodium hydroxide aqueous solution and then with 200 mL of water, and separated, .The obtained organic layer was concentrated under reduced pressure to obtain a crude product of a pyridine methanol compound. 840 mL of isopropyl acetate was added to the crude product of the pyridine methanol compound and heated to 60 ° C. to dissolve the crude product, and then 840 mL of heptane was added dropwise at an internal temperature of 50 ° C. or higher.The solution was cooled to 5 ° C., the slurry of the pyridine methanol compound was aged at around 5 ° C. for 2 hours, and the slurry solution was filtered by vacuum filtration.The filtered crystals were washed with a mixed solution of 60 mL of isopropyl acetate and 60 mL of heptane, and then the obtained white crystals were dried under reduced pressure at 40 ° C. for 5 hours,102 g (363 mol, production yield: 89.9percent) of a pyridine methanol compound was obtained as white crystals (purity: 99.53percent).
89% With sodium tetrahydroborate; zinc(II) chloride In tetrahydrofuran at 60 - 85℃; for 16 h; To a 1000 ml three-necked flask, 600 ml of tetrahydrofuran, 2- (4-methyl-2-phenyl-1-piperazinyl)(134 g, 0.45 mol),Zinc chloride (306 g, 2.25 mol) was added sodium borohydride (85 g, 2.25 mol) in portions carefully. The temperature was raised to 60-85 ° C after addition and reflux with stirring for 16 hours, cooled to 0 ° C and carefully quenched with methanol The reaction mixture was removed under reduced pressure. 600 ml of 6N hydrochloric acid was added and the mixture was heated to 80 ° C with heating and stirred for 1 hour. The mixture was cooled to room temperature and extracted with methylene chloride (2 L × 3). The organic phase was dried over 1 kg of anhydrous sodium sulfate, A white solid was obtained. The white solid was further dried by blowing with air at 50 ° C to give 113 g of 1-(3-hydroxymethylpyridin-2-yl) -4-methyl-2-phenylpiperazine as a white solid in 89percent yield.
89.9% With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 3.5 h; A stirrer,In a 2 L four-necked flask equipped with a thermometer,1618 mL (1618 mmol) of a 1 mol / L lithium aluminum hydride / tetrahydrofuran solution was added,Pyridine carboxylic acid compound 120 g (404 mmol)Was dissolved in 1800 mL of tetrahydrofuran was added dropwise over 30 minutes while maintaining the internal temperature at around 25 ° C.,And the mixture was stirred at 25 ° C. for 3 hours.While cooling the reaction solution with water, 70 mL of water was added and stirred,The organic layer and the aqueous layer were separated,The obtained organic layer was washed with 70 mL of a 15 wtpercent sodium hydroxide aqueous solution,Then,Wash sequentially with 200 mL of water,And separated.The obtained organic layer was concentrated under reduced pressure,A crude product of pyridine methanol compound was obtained.To a crude product of pyridine methanol compound,840 mL of isopropyl acetate was added,Heated to 60 ° C.,After dissolving the crude product,840 mL of heptane was added dropwise at an internal temperature of 50 ° C. or higher.The solution was cooled to 5 ° C.,The slurry of the pyridine methanol compound was aged at around 5 ° C. for 2 hours,By vacuum filtration,The slurry solution was filtered.The filtered crystals were washed with a mixed solution of 60 mL of isopropyl acetate and 60 mL of heptane,The obtained white crystals were dried under reduced pressure at 40 ° C. for 5 hours,102 g (363 mol, production yield: 89.9percent) of a pyridine methanol compound as white crystals(Purity: 99.53percent, moisture content: 320 ppm).
88% With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 25℃; for 12.5 h; 5.0 g (16.8 mmol) of the pyridinecarboxylic acid obtained in Preparation Example 1 and 60 ml of tetrahydrofuran were added to a 200 ml four-necked flask equipped with a two-piece stirring blade having a diameter of 3.6 cm, and stirred at 25 ° C. To the obtained suspension, 15.7 g (50.4 mmol) of 65percent sodium bis(2-methoxyethoxy)aluminumhydride / toluene solution was added dropwise over 30 minutes while maintaining the internal temperature at around 25 ° C, and the mixture was stirred at 25 ° C for 12 hours (reaction conversion rate: 99.9percent). While cooling the reaction solution with water, a solution obtained by mixing 11.8 g of (+)-sodium potassium tartrate tetrahydrate and 17 ml of water was added and stirred, then the aqueous layer was separated and the obtained organic layer was washed with 2.6 ml of 15percent brine, and the solvent was distilled off under reduced pressure to obtain a crude product of pyridine methanol body as a pale yellow oil. 25 ml of toluene was added to the obtained oily matter and dissolved, and insoluble matter was removed by filtration and 25 ml of heptane was added to the solution, and the mixture was stirred for 5 hours. The precipitated solid was collected by filtration under reduced pressure, and the obtained wet body was dried under reduced pressure at 80 ° C for 20 hours to obtain 4.2 g of pyridine methanol body as white crystals (yield: 88percent). As a result of analyzing this crystal by HPLC, the purity of the pyridine methanol product was 99.89percent and the content of the methyl form was 0.029percent.
81% With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 40℃; for 5 h; Inert atmosphere a 1 L three-necked flask equipped with a stirring blade and a thermometer, 60 g (201.8 mmol) of a pyridine carboxylic acid compound was suspended in 270 mL of tetrahydrofuran and cooled to 10 ° C. 240 g (706.2 mmol) of a toluene solution of 70percent sodium dihydrobis (2-methoxyethoxy) aluminate was added dropwise under a nitrogen stream, and the mixture was reacted at 40 ° C. for 5 hours. After completion of the reaction, 275 mL of a 35 mass percent Rochelle salt aqueous solution was added, and the organic layer and the aqueous layer were separated. After washing by adding 120 mL of 25 mass percent saline to the organic layer, separation was performed, and the obtained organic layer was concentrated under reduced pressure. 240 mL of toluene was added to the obtained residue, and the mixture was heated to 60 to 65 ° C., and insoluble matter was filtered off. After concentrating the toluene layer under reduced pressure, 57 g of a crude product of pyridine methanol compound was obtained. (Crude yield 99percent).The rough object 57g of the aforementioned pyridinemethanol compound was added to the 1-L three necked flask furnished with an impeller and a thermometer. After having added 420 g of isopropyl acetate to this, heating at 60 degrees C and dissolving this rough object, the solution was cooled to 5 degrees C, and the slurry liquid of the pyridinemethanol compound was riped near 5 degree C for about 2 hours. The white crystals obtained by filtering the slurry solution after aging are moved to a 1L glass flask, It dried in vacuum at 40 degrees C for 2 hours, dried in vacuum by the rotating evaporator by 0.5kpa, and obtained the pyridinemethanol compound 43.5g (153.7 mol) as white crystals (76percent of yield, the HPLC purity of 99.9percent, the amount of residual solvents of 250 ppm of isopropyl acetate). The crystal coating weight to the reaction container wall surface at the time of crystallization was less than 1mass percent, and the crystal coating weight to the revolving dry inside-of-a-plane wall was also less than 1mass percent.
80% With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 10 - 40℃; for 5 h; Inert atmosphere 10.0 g (33.6 mmol) of the pyridine carboxylic acid compound obtained in Preparation Example 1 and 45 mL of tetrahydrofuran were added to a 300 mL four-necked flask equipped with a stirring blade and a thermometer to suspend them and cooled to 10 ° C. Under nitrogen atmosphere, 70percent SDMA in toluene solution 34. After 0 g (117.7 mmol) was added dropwise, the reaction was carried out at around 40 ° C. for 5 hours.After completion of the reaction, 54.0 g (67.0 mmol) of a 35 mass percent Rochelle salt aqueous solution was added, and then organic solutionThe medium layer and the aqueous layer were separated. 25 mL of a 25 mass percent sodium chloride aqueous solution was added to the organic solvent layer, and the solution was stirred by stirring at around 25 ° C. for 30 minutes, and liquid separation was carried out. The amount of the pyridine methanol compound contained in the aqueous layer obtained by liquid separation was 1.1percent based on the theoretical yield. On the other hand, the organic solvent layer obtained by liquid separation was concentrated under reduced pressure to obtain a residue. To this residue, 75 mL of tetrahydrofuran was added and after stirring for 30 minutes at around 25 ° C., insoluble matter was filtered off.The resulting tetrahydrofuran solution was concentrated under reduced pressure, 70 mL of isopropyl acetate was added to the residue, and the mixture was heated to around 60 ° C.After the residue had dissolved, 70 mL of heptane was added dropwise at 50 ° C. or more.The obtained solution was cooled to around 5 ° C. and stirred at about the same temperature for about 2 hours.The precipitated solids were separated by filtration, and the obtained wet bodies were dried under reduced pressure at 40 ° C. for 12 hours to obtain 7.6 g (26.9 mmol) of a pyridine methanol compound.(Purity: 99.90percent, production yield: 80.0percent)
76% With lithium aluminium tetrahydride In tetrahydrofuran at 5℃; for 3 h; Reflux; Inert atmosphere In a 1 L three-necked flask equipped with a stirring blade and a thermometer, 20.3 g (68.3 mmol) of the type II crystal pyridine carboxylic acid obtained in Example 1 was dissolved in 100 mL of anhydrous tetrahydrofuran, and the solution was heated to 5 ° C. After cooling, a suspension of 7.8 g (205.5 mmol) of lithium aluminum hydride diluted with 80 ml of THF was gradually added under a nitrogen stream, and the mixture was reacted under heating reflux for 3 hours. After completion of the reaction, it was cooled to 0 ° C., 82 mL of distilled water was gradually added dropwise, and the mixture was stirred at room temperature for 1 hour, and the precipitated inorganic salt was separated by filtration. The filtrate was concentrated under reduced pressure to obtain 18.2 g of a crude product of a pyridine methanol compound (crude yield 99percent, excess reduced form 0.2percent). Diethyl ether (400 mL) was added to the crude product, and after heating to 40 ° C., the mixture was cooled to 5 ° C. and recrystallized to obtain 14.5 g (51.1 mmol) of a pyridine methanol compound (yield: 76percent HPLC purity 98.7percent, excess reduced form 0.2 °percent).

References: [1] Patent: US2002/35255, 2002, A1, .
[2] Organic Preparations and Procedures International, 2007, vol. 39, # 4, p. 399 - 402.
[3] Patent: JP2017/39659, 2017, A, . Location in patent: Paragraph 0048-0049.
[4] Patent: JP2017/88565, 2017, A, . Location in patent: Paragraph 0060; 0061.
[5] Patent: JP2017/88564, 2017, A, . Location in patent: Paragraph 0056; 0057.
[6] Patent: JP2017/165689, 2017, A, . Location in patent: Paragraph 0053; 0054.
[7] Patent: CN105367571, 2017, B, . Location in patent: Paragraph 0020; 0043; 0044.
[8] Patent: JP2017/222608, 2017, A, . Location in patent: Paragraph 0053; 0054.
[9] Patent: JP2015/174853, 2015, A, . Location in patent: Paragraph 0039; 0040; 0042.
[10] Patent: JP2017/128551, 2017, A, . Location in patent: Paragraph 0063-0066.
[11] Patent: US2002/95038, 2002, A1, .
[12] Patent: JP2017/52704, 2017, A, . Location in patent: Paragraph 0055.
[13] Patent: JP2017/218411, 2017, A, . Location in patent: Paragraph 0006; 0102-0104.
[14] Patent: US6339156, 2002, B1, . Location in patent: Page column 6.
 

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Technical Information

Categories

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