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[ CAS No. 74420-15-8 ] {[proInfo.proName]}

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Chemical Structure| 74420-15-8
Chemical Structure| 74420-15-8
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Product Details of [ 74420-15-8 ]

CAS No. :74420-15-8 MDL No. :MFCD02179276
Formula : C7H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :VJDGIJDCXIEXPF-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :5523659
Synonyms :

Calculated chemistry of [ 74420-15-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.79
TPSA : 28.68 Ų

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) : -6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 2.0
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.99
Solubility : 0.203 mg/ml ; 0.00103 mol/l
Class : Soluble
Log S (Ali) : -2.23
Solubility : 1.16 mg/ml ; 0.0059 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0337 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.59

Safety of [ 74420-15-8 ]

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

Application In Synthesis of [ 74420-15-8 ]

* 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 [ 74420-15-8 ]
  • Downstream synthetic route of [ 74420-15-8 ]

[ 74420-15-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 74420-15-8 ]
  • [ 68-12-2 ]
  • [ 4649-09-6 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -70 - -10℃; for 5 h;
Stage #2: at 20℃; for 15 h;
To a suspension of 3-bromo-1H-pyrrolo[2,3-b]pyridine (9.85 g, 50.0 mmol) in THF (300 mL) was added dropwise a 2.5M solution of n-butyllithium in hexanes (42 mL, 105.0 mmol, 2.1 equiv.) at -70° C. The temperature of the reaction mixture was raised to -60° C. during the addition and became a clear solution. The resulting brick red color solution was slowly allowed to warm to -10° C. during a period of 1 h and then stirred for 4 h at this temperature. Again, the mixture was cooled to -70° C. and a solution of dimethylformamide (8.5 mL, 110.0 mmol) in THF (30 mL) was added dropwise. After addition, the mixture was allowed to warm to room temperature and stirred for 15 h. Then, the mixture was diluted with saturated ammonium chloride solution and the two layers were separated. The aqueous layer was extracted with ethyl acetate (2.x.150 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the crude brown solid which was dissolved in ethyl acetate (70 mL) at hot condition and then stored in the refrigerator overnight. The solids were collected by filtration and washed with ethyl acetate. After drying in air, 6.05 g (83percent yield) of 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde was isolated as an yellow solid: EI-HRMS m/e calcd for C8H6N2O (M+) 146.0480, found 146.0478.
Reference: [1] Patent: US2006/84674, 2006, A1, . Location in patent: Page/Page column 6-7
  • 2
  • [ 271-63-6 ]
  • [ 74420-15-8 ]
YieldReaction ConditionsOperation in experiment
99% at 100℃; for 3 h; Reflux 100mmol 7-azaindole was dissolved in organic solvent. Add into a reaction kettle. Add 40mmol catalyst. Maintain the temperature at 100 °C. 90 rpm/min of stirring. Place 300mmol bromine gas. Reflux reaction for 3h. Afterwards, completion of the reaction, purification to obtain 3-bromo-7-azaindole. Wherein the catalyst is nickel(II) acetate and triethanolamine boratemole ratio of 3:1 mixture. The yield of the product is 99.0percent
93% With N-Bromosuccinimide In dichloromethane at 0 - 20℃; for 16 h; Inert atmosphere 4.2.19
3-Bromo-1H-pyrrolo[2,3-b]pyridine (13)
In a heat dried and nitrogen purged round bottom flask, 1 (1.00 g, 8.46 mmol) was dissolved in CH2Cl2 (20 mL) and cooled in an ice bath, then N-bromosuccinimide (1.66 g, 9.31 mmol) was added.
The mixture was left to warm up to room temperature overnight under nitrogen atmosphere.
The reaction mixture was diluted with CH2Cl2 and washed with a saturated sodium hydrogenocarbonate solution.
The aqueous layer was extracted three times with EtOAc and the gathered organic layers were washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give 1.79 g of a brown solid.
The crude product was purified by chromatography on silica gel column, cyclohexane/EtOAc 1:1, to give 1.56 g of the expected product as a light brown solid in 93percent yield. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 11.45 (br, 1H), 8.38 (dd, J = 1.2, 5.1 Hz, 1H), 8.06 (dd, J = 1.2, 7.8 Hz, 1H), 7.48 (s, 1H), 7.28 (dd, J = 5.1, 7.8 Hz, 1H).
13C NMR (75 MHz, DMSO-d6) δ (ppm): 145.0, 140.9, 130.2, 125.6, 121.5, 116.3, 89.9.
89.6% With bromine In N,N-dimethyl-formamide at 0 - 10℃; for 2.66667 h; Large scale [0379] Example 1: 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l-tosyl-lH- pyrrolo[2,3-b]pyridine (la) [0380] Example la: 3-bromo-lH-pyrrolo[2,3-b]pyridine (6a) [0381] 7-azaindole (5a) (6.9 kg, 58.4 moles) was added to a 200L glass-lined reactor containing 52.6 kg DMF. A solution of Br2 in DMF (9.7 kg Br2 in 14.7 kg DMF) was added drop wise to maintain the mixture temperature of about 0-10 °C. After the addition was complete, the temperature was maintained at about 0-10 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the 7-azaindole was less than 3percent (after about 2 hours and 40 minutes). [0382] The reaction was quenched with 10percent aqueous solution of NaHSC>3 (17.5 kg) while maintaining the temperature below 15 °C. A saturated aqueous solution of NaHCC>3 (61.6 kg) below 25 °C was added to adjust the pH to about 7 to 8. After neutralization, the mixture was transferred into a 50 L vacuum filter and filtered. The resultant cake was washed with water (18 kg) and then petroleum ether (12 kg). The cake was dried in a tray dryer at about 50-60 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.8percent. A yellow solid resulted (10.3 kg, 99.1percent purity as measured by HPLC (method A), 89.6percent yield of 3-bromo-lH-pyrrolo[2,3-b]pyridine (6a)).
89.6% With bromine In N,N-dimethyl-formamide at 0 - 10℃; for 2.66667 h; Large scale [00383] 3-bromo-lH-pyrrolo[2, 3-bJpyridine: [00384] Commercially available 7-Azaindole (6.9 kg, 58.4 moles) was added to a 200L glass-lined reactor containing 52.6 kg DMF. A solution of Br2 in DMF (9.7 kg Br2 in 14.7 kg DMF) was added drop wise to maintain the mixture temperature of about 0-10 °C. After the addition was complete, the temperature was maintained at about 0-10 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the 7-azaindole was less than 3percent (after about 2 hours and 40 minutes). Typical retention time for 3-bromo-lH-pyrrolo[2,3-b]pyridine was 3.228 minutes. [00385] The reaction was quenched with 10percent aqueous solution of NaHS03 (17.5 kg) while maintaining the temperature below 15 °C. A saturated aqueous solution of NaHC03 (61.6 kg) below 25 °C was added to adjust the pH to about 7 to 8. After neutralization, the mixture was transferred into a 50L vacuum filter and filtered. The resultant cake was washed with water (18 kg) and then petroleum ether (12 kg). The cake was dried in a tray dryer at about 50-60 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.8percent. A yellow solid resulted (10.3 kg, 99.1percent purity as measured by HPLC (method A), 89.6percent yield of 3-bromo-lH-pyrrolo[2,3-b]pyridine).
89.6% With bromine In N,N-dimethyl-formamide at 0 - 10℃; for 2.66667 h; Large scale [0268] 3-bromo-l H-pyrrolo[2, 3-b]pyridine: [0269] Commercially available 7-Azaindole (6.9 kg, 58.4 moles) was added to a 200L glass-lined reactor containing 52.6 kg DMF. A solution of Br2 in DMF (9.7 kg Br2 in 14.7 kg DMF) was added drop wise to maintain the mixture temperature of about 0-10 °C. After the addition was complete, the temperature was maintained at about 0-10 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the 7-azaindole was less than 3percent (after about 2 hours and 40 minutes). Typical retention time for 3-bromo-lH-pyrrolo[2,3-b]pyridine was 3.228 minutes. [0270] The reaction was quenched with 10percent aqueous solution of NaHS03 (17.5 kg) while maintaining the temperature below 15 °C. A saturated aqueous solution of NaHC03 (61.6 kg) below 25 °C was added to adjust the pH to about 7 to 8. After neutralization, the mixture was transferred into a 50L vacuum filter and filtered. The resultant cake was washed with water (18 kg) and then petroleum ether (12 kg). The cake was dried in a tray dryer at about 50-60 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.8percent. A yellow solid resulted (10.3 kg, 99.1percent purity as measured by HPLC (method A), 89.6percent yield of 3-bromo-lH-pyrrolo[2,3-b]pyridine).
89.6% With bromine In N,N-dimethyl-formamide at 0 - 10℃; for 2.66667 h; Large scale [0390] 3-bromo-1H-pyrrolo[2,3-b]pyridine: [0391] Commercially available 7-Azaindole (6.9 kg, 58.4 moles) was added to a 200 L glass-lined reactor containing 52.6 kg DMF. A solution of Br2 in DMF (9.7 kg Br2 in 14.7 kg DMF) was added drop wise to maintain the mixture temperature of about 0-10 °C. After the addition was complete, the temperature was maintained at about 0-10 °C. The completeness of the reaction was measured by HPLC (method A) with sample aliquots after 30 minutes. The reaction was considered complete when the 7-azaindole was less than 3percent (after about 2 hours and 40 minutes). Typical retention time for 3-bromo-lH-pyrrolo[2,3-b]pyridine was 3.228 minutes. [0392] The reaction was quenched with 10percent aqueous solution of NaHS03 (17.5 kg) while maintaining the temperature below 15 °C. A saturated aqueous solution of NaHC03 (61.6 kg) below 25 °C was added to adjust the pH to about 7 to 8. After neutralization, the mixture was transferred into a 50 L vacuum filter and filtered. The resultant cake was washed with water (18 kg) and then petroleum ether (12 kg). The cake was dried in a tray dryer at about 50-60 °C until the water content detected by KF (Karl Fisher reaction) was less than 0.8percent. A yellow solid resulted (10.3 kg, 99.1percent purity as measured by HPLC (method A), 89.6percent yield of 3-bromo-lH-pyrrolo[2,3-b]pyridine).
85% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In 1,4-dioxane at 10℃; General procedure: DBDMH (157 mg, 0.55 mmol) was added in five potion to a solution ofindoles (1.0 mmol) in dioxane at 10 °C over two minutes with stir, and the resulting solution was stirred for 5to 10 minutes. TLC indicate that the reaction is completed. The reactionsolution was poured into the saturated NaHCO3 solution (10 mL), themixtures was extracted by ethyl acetate (15 mL*2). The organic phase was dried over Na2SO4,filtered, concentrated under reduced pressure. The residue was then purified byflash chromatography on 200~300 mesh silica gel to provide the correspondingproduct 2.
82% With bromine In chloroform at 0 - 20℃; for 1 h; Azaindole 1 (4g, 0.025 mol) in 100 mL of chloroform was cooled to 0°C. Bromine in 20 mL of chloroform was added dropwise the resulting mixture was stirred at 0°C for 1 h. The resulting suspension was diluted with 0.5N HCl and the aqueous layer was made basic with 0.5 N NaOH and the solid filtered to provide 4g (82percent) of crude product 2 that was used directly for the next step.
75% With N-Bromosuccinimide; sulfuric acid In tetrahydrofuran at 20℃; for 48 h; To a solution of 7-azaindole (5 g, 42.2 mmol) in THF (400 mL) were added first the solid N-bromosuccinimide (8 g, 45.0 mmol) then 20 drops of conc. sulfuric acid at room temperature. While stirring some suspension was formed during 2 days. The mixture was diluted with saturated ammonium chloride solution and the two layers were separated. The aqueous layer was extracted with ethyl acetate (4.x.150 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the crude yellow solid. This solid was dissolved in ethyl acetate (100 mL) at hot condition and then stored in the refrigerator overnight. The solids were collected by filtration and washed with ethyl acetate. After drying in air, 6.2 g (75percent yield) of 3-bromo-1H-pyrrolo[2,3-b]pyridine was isolated as an yellow solid: EI-HRMS m/e calcd for C7H5BrN2 (M+) 195.9636, found 195.9636.
72% With bromine In tetrachloromethane at 20℃; for 12 h; Inert atmosphere 10.0 g (84.65 mmol) of 7-azaindole was suspended in 300 ml of CCl 4 and 4.35 mL (84.65 mmol) of Br 2 slowly at room temperatureAnd stirred for 12 hours under a stream of nitrogen. After completion of the reaction, the resulting solid was filtered,The reaction mixture was dissolved in loromethane and extracted with Na2S2O3. The organic solvent was removed and dried to obtain 12.0 g (yield: 72percent) of the intermediate product (A)
72% With bromine In tetrachloromethane; chloroform at 0℃; for 0.5 h; lH-Pyrrolo[2,3-b]pyridine (5.0 grams, 42.29 mmol) was dissolved in chloroform (67 ml) under a nitrogen atmosphere and chilled to 0 0C, Bromine (2.17 ml, 42.29 mmol) diluted in carbon tetrachloride (85 ml) was added dropwise via addition funnel. The reaction was stirred for an additional 30 minutes at 0 0C and water (100 ml) was added, the aqueous layer was separated, filtered, basified with 5N NaOH to pH 11, and the precipitate collected by filtration to yield Compound 25.1 (6.02 grams, 35.12 mmol). ES (+) MS m/e = 199 (M+2).
58% With bromine In tetrachloromethane at 0℃; for 2 h; 7-azaindole (5.000 g, 42.32 mmol) was added to carbon tetrachloride (150 mL) at 0 . To the mixture, bromine (2.182 mL, 42.32 mmol) was added, followed by stirring at the same temperature for 2 hours. Then, 0.5 N hydrochloric acid aqueous solution (500 mL) was added to the reaction mixture, followed by extraction. To the water layer, 0.5 N sodium hydroxide aqueous solution (700 mL) was added, followed by stirring. The precipitated solid was filtered, washed with water, and then dried to afford the title compound (4.820 g, 58percent) as a brown solid.
1.55 g With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h; Inert atmosphere The solution of 1H-pyrrolo[2,3-b]pyridine (1.0 g, 1 equiv.) in DMF (30 mL) at 0 oc wastreated portionwise with NBS ( 1. 51 g, 1 equiv.) under argon, and the resulting solution was20 stirred at 0 oc for 20 min. The reaction mixture was allowed to warm toRT and stirringwas continued for 10 min. Then, the reaction mixture was transferred to a separatoryfunnel containing distilled water, and extracted with EtOAc (2 x 150 mL). The combinedorganic extracts were dried over Na2S04, filtered, and solvent was removed in vacuo.Crude product was recrystallized from DCM to afford the expected product (1.55 g).25 LCMS: MW (calcd): 197.03; MS (ES+, m/z): 197.3, 199.3 [M+H

Reference: [1] Patent: CN106349242, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035; 0036; 0037; 0038
[2] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[3] Patent: WO2013/6634, 2013, A2, . Location in patent: Paragraph 0379-0382
[4] Patent: WO2013/70606, 2013, A1, . Location in patent: Paragraph 00383-00385
[5] Patent: WO2014/74471, 2014, A1, . Location in patent: Paragraph 0268-0270
[6] Patent: WO2014/201332, 2014, A1, . Location in patent: Paragraph 0390-0392
[7] Tetrahedron Letters, 2015, vol. 56, # 9, p. 1096 - 1098
[8] Organic Letters, 2015, vol. 17, # 12, p. 2886 - 2889
[9] Patent: WO2005/95400, 2005, A1, . Location in patent: Page/Page column 326; 327
[10] Patent: US2006/84674, 2006, A1, . Location in patent: Page/Page column 6
[11] Patent: KR2015/15252, 2015, A, . Location in patent: Paragraph 0178;0179
[12] Patent: WO2008/5457, 2008, A2, . Location in patent: Page/Page column 71
[13] Synlett, 2007, # 2, p. 211 - 214
[14] Patent: WO2015/102426, 2015, A1, . Location in patent: Paragraph 1083-1085
[15] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 12, p. 1124 - 1129
[16] Journal of the Chemical Society [Section] C: Organic, 1969, p. 1505 - 1514
[17] Journal of the American Chemical Society, 1956, vol. 78, p. 1247,1249
[18] Patent: US2006/100218, 2006, A1, . Location in patent: Page/Page column 51
[19] Patent: US2011/15173, 2011, A1, . Location in patent: Page/Page column 30
[20] Patent: US2011/257187, 2011, A1, . Location in patent: Page/Page column 21
[21] Patent: US2011/257189, 2011, A1, . Location in patent: Page/Page column 34-35
[22] European Journal of Medicinal Chemistry, 2016, vol. 114, p. 220 - 231
[23] Patent: WO2018/78360, 2018, A1, . Location in patent: Page/Page column 147
  • 3
  • [ 74420-15-8 ]
  • [ 24424-99-5 ]
  • [ 226085-17-2 ]
YieldReaction ConditionsOperation in experiment
79% at -20 - 20℃; for 2 h; To a solution of 3-bromo-1-H-pyrrolo[2,3-b]pyridine (0.10 g, 0.50 mmol) in THF (4.0 mL) under nitrogen atmosphere was added DMAP (0.006 g, 0.06 mmol). The resulting reaction mixture was cooled to -2O0C followed by addition of Boc anhydride (122 μL, 0.56 mmol). The reaction mixture ws then allowed to warm upto room temperature and stirred for 2 h. After the completion of reaction (TLC monitoring), water (20 mL) was added to the reaction mixture and then extracted with EtOAc (3 x 50 mL). The combined organics was dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (60-120 M, 5percent EtOAc-Hexane) to obtain the desired product as oily mass (0.12 g, 79percent).
Reference: [1] Synthesis, 1999, # 4, p. 615 - 620
[2] Patent: WO2009/74812, 2009, A1, . Location in patent: Page/Page column 59
  • 4
  • [ 74420-15-8 ]
  • [ 4637-24-5 ]
  • [ 281192-91-4 ]
Reference: [1] Synlett, 2013, vol. 24, # 5, p. 570 - 574
  • 5
  • [ 74420-15-8 ]
  • [ 98-09-9 ]
  • [ 880769-95-9 ]
YieldReaction ConditionsOperation in experiment
98%
Stage #1: With tetrabutylammomium bromide; sodium hydroxide In dichloromethane
Stage #2: at 0 - 20℃; for 1 h;
4.2.20
3-Bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (14)
In a heat dried and nitrogen purged round bottom flask, 13 (175 mg, 0.89 mmol), tetrabutylammonium bromide (10 mg, 0.03 mmol), finely grounded sodium hydroxide (107 mg, 2.67 mmol) and CH2Cl2 (5 mL) were mixed, stirred and cooled down to 0 °C in an ice bath, then benzene sulfonyl chloride (0.142 mL, 1.11 mmol) was added slowly.
The mixture was left to warm up to room temperature and was stirred at this temperature for 1 h.
The reaction was hydrolyzed with water (6 mL) and extracted by CH2Cl2 (twice).
The organic layer was washed with water and a saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure to give an orange solid.
The crude product was triturated in pentane, filtered, washed with pentane and dried to give 294 mg of the expected product as an orange solid in 98percent yield. 1H NMR (300 MHz, CDCl3) δ (ppm): 8.48 (dd, J = 1.5, 4.8 Hz, 1H), 8.24-8.17 (m, 2H), 7.82 (dd, J = 1.5, 8.0 Hz, 1H), 7.79 (s, 1H), 7.60 (dd, J = 7.5 Hz, 1H), 7.54-7.46 (m, 2H), 7.27 (dd, J = 4.8, 8.0 Hz, 1H).
47% With potassium carbonate In acetone Step 2-Preparation of 1-benzenesulfonyl-3-bromo-1H-pyrrolo[2,3-b]pyridine 4
3-Bromo-1H-pyrrolo[2,3-b]pyridine (3, 280 mg, 1.4 mmol) was dissolved in acetone (15 mL) and potassium carbonate (220 mg, 1.6 mmol) was added, followed by benzenesulfonyl chloride (0.2 mL, 1.6 mmol).
The reaction mixture was heated to reflux overnight, filtered and concentrated under reduced pressure.
The resulting solid was purified by flash chromatography (5percent-20percent ethyl acetate:hexanes) to provide the desired product, 4, (300 mg, 47percent). MS(ESI) [M+H+]+=455.0.
Step 3-Preparation of 1-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine 5
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[2] Patent: US2006/100218, 2006, A1, . Location in patent: Page/Page column 52
[3] Patent: US2011/15173, 2011, A1, . Location in patent: Page/Page column 30
[4] Patent: US2011/257187, 2011, A1, . Location in patent: Page/Page column 21-22
[5] Patent: US2011/257189, 2011, A1, . Location in patent: Page/Page column 35
  • 6
  • [ 74420-15-8 ]
  • [ 886547-94-0 ]
Reference: [1] Patent: US2011/257187, 2011, A1,
[2] Patent: US2011/257189, 2011, A1,
  • 7
  • [ 74420-15-8 ]
  • [ 866545-91-7 ]
Reference: [1] Patent: WO2013/6634, 2013, A2,
[2] Patent: WO2013/70606, 2013, A1,
[3] Patent: WO2014/74471, 2014, A1,
[4] Patent: WO2014/201332, 2014, A1,
[5] Patent: KR2015/15252, 2015, A,
  • 8
  • [ 74420-15-8 ]
  • [ 882562-39-2 ]
Reference: [1] Patent: WO2013/6634, 2013, A2,
[2] Patent: WO2013/70606, 2013, A1,
[3] Patent: WO2014/74471, 2014, A1,
[4] Patent: WO2014/201332, 2014, A1,
  • 9
  • [ 74420-15-8 ]
  • [ 944842-54-0 ]
Reference: [1] Patent: WO2013/6634, 2013, A2,
[2] Patent: WO2013/70606, 2013, A1,
[3] Patent: WO2014/74471, 2014, A1,
[4] Patent: WO2014/201332, 2014, A1,
  • 10
  • [ 74420-15-8 ]
  • [ 944842-54-0 ]
Reference: [1] Patent: WO2013/6634, 2013, A2,
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