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Quality Control of [ 871836-51-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 871836-51-0 ]

SDS Specification

Alternatived Products of [ 871836-51-0 ]

Product Details of [ 871836-51-0 ]

CAS No. :	871836-51-0	MDL No. :	MFCD11870058
Formula :	C₆H₄ClN₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FUXZQGSDRGDYGX-UHFFFAOYSA-N
M.W :	153.57	Pubchem ID :	46835637
Synonyms :

Calculated chemistry of [ 871836-51-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.9
TPSA :	41.57 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.65
Log Po/w (XLOGP3) :	1.44
Log Po/w (WLOGP) :	1.61
Log Po/w (MLOGP) :	0.78
Log Po/w (SILICOS-IT) :	2.24
Consensus Log Po/w :	1.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.37
Solubility :	0.662 mg/ml ; 0.00431 mol/l
Class :	Soluble
Log S (Ali) :	-1.92
Solubility :	1.85 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.14
Solubility :	0.112 mg/ml ; 0.000728 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.45

Safety of [ 871836-51-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 871836-51-0 ]

* 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.

Downstream synthetic route of [ 871836-51-0 ]

[ 871836-51-0 ] Synthesis Path-Downstream 1~21

1
[ 871836-50-9 ]
[ 871836-51-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; at 110℃; for 18h;	A solution of 1H-pyrazolo[4,3-c]pyridine N-oxide (0.4 g, 3 mmol) in phosphorous oxychloride (10 mL) was heated at 110 °C for 18 hours. The cool reaction mixture was evaporated under reduced pressure and the residue carefully dissolved in water (30 mL). The solution was basified with 10 percent w/v aqueous potassium carbonate solution and extracted with ethyl acetate (3 X 50 mL). The combined organic extracts were dried (MgS04) and evaporated under reduced pressure to give the title compound as a yellow solid, 0.1 g. LRMS (APCI+): m/z [M+H]+ 154

Reference： [1]Patent: WO2005/121094,2005,A1 .Location in patent: Page/Page column 52

2
[ 871836-50-9 ]
[ 871836-51-0 ]
[ 1206979-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; for 3h;Heating / reflux;	(2) To the compound obtained in the above step (1) (1.4 g) was added phosphorus oxychloride (30 mL) and the mixture was refluxed under heating for 3 hours. The reaction mixture was concentrated and to the residue was added an aqueous saturated sodium hydrogencarbonate solution. The mixture was extracted with ethyl acetate and the extract was dried over magnesium sulfate and concentrated to give a mixture of 4-chloro-1H-pyrazolo[4,3-c]pyridine and 6-chloro-1H-pyrazolo[4,3-c]pyridine (0.81 g, yield: 51 percent). MS(APCI)m/z; 154/156 [M+H]+

Reference： [1]Patent: EP1772454,2007,A1 .Location in patent: Page/Page column 63

3
[ 871836-51-0 ]
[ 57260-71-6 ]
[ 946571-31-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 6-chloro-1H-pyrazolo[4,3-c]pyridine; In 1-methyl-pyrrolidin-2-one; at 140℃; for 2h;	(3) To a solution of the compound obtained in the above step (2) (0.72 g) in N-methylpyrrolidone (5.0 mL) was added N-tert-butoxycarbonylpiperazine (1.7 g) and the mixture was stirred at 140 °C for 2 hours. After cooling, to the reaction mixture was added water and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a flash column chromatography on NH-silica gel (Solvent; n-hexane/ethyl acetate = 1: 1) to give 4-[4-(tert-butoxycarbonyl)piperazin-1-yl]-1H-pyrazolo[4,3-c]pyridine (0.64 g) as colorless crystals. MS(APCI)m/z; 304 [M+H]+

Reference： [1]Patent: EP1772454,2007,A1 .Location in patent: Page/Page column 63

4
[ 871836-51-0 ]
[ 459-46-1 ]
[ 1160360-05-3 ]
[ 1160360-06-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In N,N-dimethyl-formamide; at 20℃;	To 4-chloro-1 H-pyrazolo[4,3-c]pyridine (60 mg, 0.40 mmol) in 2 ml DMF was added 4-Fluorobenzylbromide (0.060 ml, 0.48 mmol) then add NaH (20 mg, 0.4 mmol) and stir at room temperature overnight. Work up by adding water and EtOAc and extract three times with EtOAc. Pool all organics and wash one time with brine then dry over sodium sulfate, filter and concentrate to dryness. The residue was purified by chromatography over silica gel (eluted with Hexanes/EtOAc 99:1 to 50:50) to provide 38 mg of major isomer A and 15 mg of minor isomer B

Reference： [1]Patent: WO2009/73777,2009,A1 .Location in patent: Page/Page column 201

5
[ 871836-51-0 ]
[ 1190841-67-8 ]
[ 1190841-50-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5250 - 5255

6
[ 871836-51-0 ]
[ 108-91-8 ]
[ 1246347-27-2 ]

Yield	Reaction Conditions	Operation in experiment
26%	With hydrogenchloride; In water; at 190℃; for 1h;	Example 133Cyclohexyl-(1H-pyrazolo[4,3-c]pyridin-4-yl)-amineIntermediate 11 (30 mg, 0.20 mmol), cyclohexylamine (89 mul, 0.29 mmol) and cone. HCI (18 mul, 0.59 mmol) were combined in n-butanol (0.5 ml) and heated in the microwave at 190 °C for 1 h. The solvents were evaporated to dryness and the crude mixture purified by preparative LCMS to give a white solid (11 mg, 26percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 1.14 - 1.44 (m, 5 H), 1.63 - 1.71 (m, 1 H), 1.73 - 1.83 (m, 2 H), 1.96 - 2.06 (m, 2 H), 4.04 (m, 1 H)1 6.61 (d, J=6.0 Hz, 1 H), 7.01 (d, J=7.8 Hz, 1 H), 7.70 (d, J=6.0 Hz, 1 H), 8.24 (s, 1 H); m/z (ES+APCI)+: 217 [M + H]+.

Reference： [1]Patent: WO2010/106333,2010,A1 .Location in patent: Page/Page column 140

7
[ 372-19-0 ]
[ 871836-51-0 ]
[ 1246347-26-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	With hydrogenchloride; In water; butan-1-ol; at 190℃; for 1h;	Example 132(3-Fluoro-phenyl)-(1H-pyrazolo[4,3-c]pyridin-4-yl)-amineIntermediate 11 (30 mg, 0.20 mmol), 3-fluoroaniline (28 mul, 0.29 mmol) and cone. HCI (aq) (18 mul, 0.59 mmol) were combined in n-butanol (0.5 ml) and heated in the microwave at 190 °C for 1 h. The solvents were evaporated to dryness and the crude mixture purified by preparative LCMS to give a white solid (21 mg, 47percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 6.79 (td, J=8.4, 2.5 Hz, 1 H)1 7.01 (d, J=7.3 Hz, 1 H), 7.33 - 7.41 (m, 1 H)1 7.62 (d, J=7.3 Hz, 1 H), 7.95 (d, J=6.0 Hz, 1 H)1 8.16 (dt, J=12.6, 2.4 Hz1 1 H)1 8.50 (s, 1 H)1 9.53 (S, 1 H); m/z (ES+APCI)+: 229 [M + H]+.

Reference： [1]Patent: WO2010/106333,2010,A1 .Location in patent: Page/Page column 140

8
[ 871836-51-0 ]
[ 1246349-99-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-Bromosuccinimide; In acetonitrile; for 3h;Reflux;	Intermediate 153-Bromo-<strong>[871836-51-0]4-chloro-1H-pyrazolo[4,3-c]pyridine</strong>N-bromosuccinimide (1.87 g, 10.5 mmol) was added to a solution of Intermediate 11 (1.61 g, 10.5 mmol) in acetonitrile (50 ml), and the mixture was heated to reflux for 3 h. The solvents were evaporated and DCM (60 ml) was added to the crude solid and the mixture stirred at r.t. for 30 min. The beige solid was filtered off, washed with DCM, then dried under vacuum (1.98 g, 81percent). 1H NMR (400 MHz, DMSO-c/6) delta ppm 7.69 (d, J=6.0 Hz, 1 H), 8.22 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 232 / 234 / 236 [M + H]+.

Reference： [1]Patent: WO2010/106333,2010,A1 .Location in patent: Page/Page column 80

9
[ 871836-51-0 ]
[ 1186647-69-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With iodine; potassium hydroxide; In 1,4-dioxane; at 75℃; for 4h;	A solution of <strong>[871836-51-0]4-chloro-1H-pyrazolo[4,3-c]pyridine</strong> (1.5 g, 9.77 mmol, 1.00 equiv), 1,4-dioxane(25 mL), potassium hydroxide (2.0 g, 35.65 mmol, 3.60 equiv), and iodine (4.95 g, 19.50 mmol,2.00 equiv) was stuffed for 4 h at 75 °C. The reaction was quenched by saturated aqueous sodium thiosulfate pentahydrate and the solids were collected by filtration. This resulted in 2.5 g (92percent) of the title compound as a light yellow solid. LC-MS (ES, mlz): 280 [M+H].
85%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 100℃;	To a solution of 4-chloro-lH-pyrazolo[4,3-c]pyridine (5.5 g, 36 mmol) in DMF (50 mL) was added NIS (6.9 g, 69 mmol). The resulted mixture was stirred at 100 °C overnight. Then the mixture was cooled and diluted with water, the precipitate was collected by filtration and dried to to give 4-chloro-3-iodo-lH-pyrazolo[4,3-c]pyridine (8.5 g, 85percent) as a light yellow solid.
72%	With iodine; potassium hydroxide; In 1,4-dioxane; at 75℃; for 4h;	To a mixture of 4-chloro-1H-pyrazolo [4, 3-c] pyridine (5.8 g, 38 mmol, synthesized according to WO 2010106333A1 and WO 2012038743A1) and KOH (8 g, 142 mmol) in dioxane (100 mL) at room temperature was added iodine (19 g, 76 mmol) . The reaction mixture was stirred at 75 for 4 h and then allowed to cool to room temperature. The solution was diluted with saturated Na2S2O3(aq) and the resulting precipitate was filtered and dried to give a yellow solid (4.1 g) . The filtrate was left standing for 3 days and filtration of the resulting precipitate yielded a further 3.55 g of the product. Combined yield (7.65 g, 72) .1H NMR (400 MHz, CDCl3) delta ppm 7.65 (d, J 6.0 Hz, 1H) , 8.13 (d, J 6.0 Hz, 1H) , 14.22 (s, 1H) . m/z (ESI)+: 280 [M+H]+

62%	With N-iodo-succinimide; In N,N-dimethyl-formamide; at 80℃; for 3h;	A solution of <strong>[871836-51-0]4-chloro-1H-pyrazolo[4,3-c]pyridine</strong> (102) (30 mg, 0.196 mmol) and NIS (66 mg 1.5 eq, 0.249mmol) in DMF (1 mL) was heated to 80 °C for 3 h. The mixture was concentrated in vacuo, brine (10 mL) was addedand then extracted with ethyl acetate (3 3 30 mL). The combined organic layer was washed with brine (10 mL), driedover MgSO4 and filtered. The filtrate was concentrated in vacuo to afford the desired product, 4-chloro-3-iodo-1Hpyrazolo[4,3-c]pyridine (103) (34 mg, 62percent yield) as a white solid. ESI-MS m/z : 277.85 [M - H]- .The product obtainedwas used directly in the next step without purification.
61%	With iodine; potassium hydroxide; In 1,4-dioxane; at 75℃; for 4h;	Intermediate 34-Chloro-3-iodo-1 H-pyrazolo[4, 3-c]pyridiTo a mixture of Intermediate 2 (5.8 g, 38 mmol) and KOH (8 g, 142 mmol) in dioxane (100 ml) at room temperature was added iodine (19 g, 76 mmol). The reaction mixture was stirred at 75 °C for 4 h, and then allowed to cool to room temperature. The solution was diluted with saturated Na2S203 (aq), and the resulting precipitate was filtered and dried to give a yellow solid (4.1 g). The filtrate was left standing for 3 days and filtration of the resulting precipitate yielded a further 2.35 g of the product. Combined yield (6.45 g, 61percent). 1 H NMR (400 MHz, DMSO-d6) delta ppm 7.64 (d, J=6.0 Hz, 1 H), 8.11 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 280 [M + H]+.
61%	With iodine; potassium hydroxide; In 1,4-dioxane; at 75℃; for 4h;	Intermediate 124-Chloro-3-iodo-1H-pyrazolo[4,3-c]pyridineTo a mixture of Intermediate 11 (5.8 g, 38 mmol) and KOH (8 g, 142 mmol) in dioxane (100 ml) at room temperature was added iodine (19g, 76 mmol). The reaction mixture was stirred at 750C for 4 h, and then allowed to cool to room temperature. The solution was diluted with saturated Na2S2O3 (aq), and the resulting precipitate was filtered and dried to give a yellow solid (4.1 g). The filtrate was left standing for 3 days and filtration of the resulting precipitate yielded a further 2.35 g of the product. Combined yield (6.45 g, 61percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.64 (d, J=6.0 Hz, 1 H), 8.11 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 280 [M + H]+.
6.3 g	With iodine; potassium hydroxide; In 1,2-dimethoxyethane; at 75℃; for 4h;	C) 4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine [1033] To a mixture of <strong>[871836-51-0]4-chloro-1H-pyrazolo[4,3-c]pyridine</strong> (4.0 g) and potassium hydroxide (4.4 g) in DME (50 mL) was added iodine (13.3 g) at room temperature. The reaction mixture was stirred at 75°C for 4 hr. The reaction mixture was added to aqueous sodium thiosulfate solution, and the mixture was left stand overnight, and the resulting solid was collected by filtration to give the title compound (6.3 g). MS(ESI+): [M+H]+ 279.9. MS(ESI+), found: 280.1.
1.57 g	With iodine; potassium hydroxide; In 1,4-dioxane; at 75℃; for 4h;	A solution of 4-chloro-lH-pyrazolo[4,3-c]pyridine (750.0 mg, 4.902 mmol, 1.0 eq), KOH (988.0 mg, 17.647 mmol, 4.0 eq) and 12 (2.49 g, 9.804 mmoL, 2.0 eq) in 1,4- dioxane (20.0 mL) was stirred at 75 °C for 4 h, then cooled and quenched by sat. aq. Na2S03 and the precipitate was collected by filtration to provide 4-chloro-3-iodo-lH- pyrazolo[4,3-c]pyridine (1.57 g).

Reference： [1]Patent: WO2015/25025,2015,A1 .Location in patent: Page/Page column 171; 328; 333
[2]Patent: WO2016/210165,2016,A1 .Location in patent: Page/Page column 67
[3]Patent: WO2017/215600,2017,A1 .Location in patent: Page/Page column 32-33
[4]Patent: EP2252293,2018,B1 .Location in patent: Paragraph 0257; 0259
[5]Patent: WO2012/38743,2012,A1 .Location in patent: Page/Page column 82
[6]Patent: WO2010/106333,2010,A1 .Location in patent: Page/Page column 78-79
[7]Patent: EP2857400,2015,A1 .Location in patent: Paragraph 1033
[8]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00619

10
[ 134031-24-6 ]
[ 871836-51-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With hydrazine hydrate; In 1,2-dimethoxyethane; at 20 - 75℃;	Intermediate 24-Chlora-1 H-pyrazolo[4, 3-c]pyridineTo a solution of Intermediate 1 (1.7 g, 9.7 mmol) in dimethoxyethane (12 ml) at room temperature was added hydrazine monohydrate (1.2 ml, 38.6 mmol) and the resulting mixture was stirred at 75 °C overnight. The mixture was then concentrated to dryness and the crude residue was purified by flash chromatography, eluting with 20 to 100percent ethyl acetate/petroleum ether gradient to give a white solid (0.82 g, 56percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.60 (d, J=6.9 Hz, 1 H), 8.14 (d, J=6.0 Hz, 1 H), 8.32 (s, 1 H); m/z (ES+APCI)+: 154 [M + H]+.
56%	With hydrazine hydrate; In 1,2-dimethoxyethane; at 20 - 75℃;	Intermediate 114-Chloro-1H-pyrazolo[4,3-c]pyridineTo a solution of Intermediate 11 (1.7 g, 9.7 mmol) in dimethoxyethane (12 ml) at room temperature was added hydrazine monohydrate (1.2 ml, 38.6 mmol) and the resulting mixture was stirred at 75 0C overnight. The mixture was then concentrated to dryness and the crude residue was purified by flash chromatography, eluting with 20 to 100percent ethyl acetate/petroleum ether gradient to give a white solid (0.82 g, 56percent). 1H NMR (400 MHz, DMSO-d6) delta ppm 7.60 (d, J=6.9 Hz, 1 H), 8.14 (d, J=6.0 Hz, 1 H), 8.32 (s, 1 H); m/z (ES+APCI)+: 154 [M + H]+.
54.4%	With hydrazine; In 1,2-dimethoxyethane; at 80℃; for 2h;	A mixture of 2 4-dichloronicotinaldehyde (800 mg 4.55 mmol) and hydrazine (364 mg 9.09 mmol) in DME (10 mL) was stirred at 80 for 2 h the solvent was concentrated and the residue was purified by column chromatography (DCMMeOH201 800 mL) to provide 4-chloro-1H-pyrazolo [4 3-c] pyridine (400 mg 2.474 mmol 54.4yield) 1HNMR(400 MHz CDCl3) delta 13.85 (m 1H) 8.31 (s 1H) 8.13 (d J5.6 Hz 1H) 7.60 (d J5.6 Hz 1H) ES-LCMS m/z 154.0 (M+H)

4 g	With hydrazine hydrate; In 1,2-dimethoxyethane; at 75℃;	B) 4-chloro-1H-pyrazolo[4,3-c]pyridine [1032] To a solution of 2,4-dichloropyridine-3-carbaldehyde (7.0 g) in DME (70 mL) was added hydrazine monohydrate (8.0 g) at room temperature. The reaction mixture was stirred overnight at 75°C, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (4.0 g). 1H NMR (400 MHz, DMSO-d6) delta 7.60 (1H, d, J = 6.0 Hz), 8.14 (1H, d, J = 6.0 Hz), 8.33 (1H, s), 13.89 (1H, brs).
1.35 g	With hydrazine hydrate; In 1,2-dimethoxyethane; at 0 - 75℃; for 16h;	To a stuffed solution of 2,4?dichloronicotinaldehyde (8.5 g, 48.29 mmol) in DME (60 mL) was added hydrazine hydrate (9.38 mL, 193.18 mmol) at 0 °C slowly and the resultant reaction mixture was heated at 75 °C for 16 h. The reaction was monitored by TLC. After completion of reaction, the reaction mixture was quenched using ice-cold water (200 mL). The aq. layer was then extracted with EtOAc (2x300 mL). The combined organic layers were washed with water (400 mL), brine (100 mL), dried over Na2SO4 and concentrated. The crude compound was purified by silica-gel (230-400) column chromatography, compound eluting at 20percent EtOAc hexane to afford 4-chloro-1H-pyrazolo[4,3-c]pyridine (1.35 g) as a light brown solid.

Reference： [1]Patent: WO2012/38743,2012,A1 .Location in patent: Page/Page column 82
[2]Patent: WO2010/106333,2010,A1 .Location in patent: Page/Page column 78-79
[3]Patent: WO2016/37578,2016,A1 .Location in patent: Page/Page column 118
[4]Patent: EP2857400,2015,A1 .Location in patent: Paragraph 1032
[5]Patent: WO2015/58084,2015,A1 .Location in patent: Paragraph 0403

11
[ 26452-80-2 ]
[ 871836-51-0 ]

Reference： [1]Patent: EP2857400,2015,A1
[2]Patent: WO2015/58084,2015,A1
[3]Patent: WO2012/38743,2012,A1
[4]Patent: WO2010/106333,2010,A1

12
[ 871836-51-0 ]
[ 1246349-97-2 ]

Reference： [1]Patent: WO2017/215600,2017,A1
[2]Patent: WO2012/38743,2012,A1

13
[ 871836-51-0 ]
[ 1246349-98-3 ]

Reference： [1]Patent: WO2012/38743,2012,A1
[2]Patent: WO2010/106333,2010,A1

14
[ 871836-51-0 ]
[ 1246348-26-4 ]