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Product Details of [ 2458-12-0 ]

CAS No. :2458-12-0 MDL No. :MFCD00007742
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XKFIFYROMAAUDL-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :75568
Synonyms :
Chemical Name :3-Amino-4-methylbenzoic acid

Calculated chemistry of [ 2458-12-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.77
TPSA : 63.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.97 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.15
Log Po/w (XLOGP3) : 0.35
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.95
Consensus Log Po/w : 0.79

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.34
Solubility : 6.98 mg/ml ; 0.0462 mol/l
Class : Very soluble
Log S (Ali) : -1.24
Solubility : 8.62 mg/ml ; 0.057 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.78
Solubility : 2.5 mg/ml ; 0.0166 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 2458-12-0 ]

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

Application In Synthesis of [ 2458-12-0 ]

* 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.

  • Upstream synthesis route of [ 2458-12-0 ]
  • Downstream synthetic route of [ 2458-12-0 ]

[ 2458-12-0 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 540-80-7 ]
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  • [ 704-91-6 ]
Reference: [1] Patent: US4898863, 1990, A,
[2] Patent: EP242167, 1991, B1,
  • 2
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  • [ 704-91-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248
[2] Patent: CN105693520, 2016, A,
[3] Patent: EP3067351, 2016, A1,
  • 3
  • [ 2458-12-0 ]
  • [ 5162-82-3 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 5, p. 1333 - 1337
  • 4
  • [ 186581-53-3 ]
  • [ 2458-12-0 ]
  • [ 151-50-8 ]
  • [ 35066-32-1 ]
Reference: [1] Helvetica Chimica Acta, 1972, vol. 55, # 1, p. 198 - 205
  • 5
  • [ 96-98-0 ]
  • [ 2458-12-0 ]
Reference: [1] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1980, vol. 16, # 3, p. 275 - 277[2] Khimiya Geterotsiklicheskikh Soedinenii, 1980, vol. 16, # 3, p. 366 - 368
[3] Zeitschrift fuer Chemie, 1869, p. 104
[4] Chemische Berichte, 1893, vol. 26, p. 1733
[5] Chemische Berichte, 1925, vol. 58, p. 1784
[6] Helvetica Chimica Acta, 1972, vol. 55, # 1, p. 198 - 205
[7] Collection of Czechoslovak Chemical Communications, 1977, vol. 42, # 7, p. 2240 - 2245
[8] Patent: EP2345636, 2011, A1, . Location in patent: Page/Page column 22
  • 6
  • [ 6946-14-1 ]
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Reference: [1] Chem. Zentralbl., 1912, vol. 83, # I, p. 136
  • 7
  • [ 60710-80-7 ]
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Reference: [1] Chemische Berichte, 1894, vol. 27, p. 2165
  • 8
  • [ 4478-10-8 ]
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Reference: [1] Gazzetta Chimica Italiana, 1888, vol. 18, p. 303
  • 9
  • [ 859816-42-5 ]
  • [ 2458-12-0 ]
Reference: [1] Gazzetta Chimica Italiana, 1888, vol. 18, p. 303
  • 10
  • [ 861525-09-9 ]
  • [ 2458-12-0 ]
Reference: [1] Chem. Zentralbl., 1912, vol. 83, # I, p. 136
  • 11
  • [ 99-94-5 ]
  • [ 2458-12-0 ]
Reference: [1] Chemische Berichte, 1893, vol. 26, p. 1733
  • 12
  • [ 90178-80-6 ]
  • [ 2458-12-0 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 2165
  • 13
  • [ 874-86-2 ]
  • [ 2458-12-0 ]
Reference: [1] Chemische Berichte, 1894, vol. 27, p. 2165
  • 14
  • [ 67-56-1 ]
  • [ 2458-12-0 ]
  • [ 18595-18-1 ]
YieldReaction ConditionsOperation in experiment
94.9% at 5℃; for 6 h; Reflux 3-amino-4-methylbenzoic acid (60.5g, 0.40mol) was dissolved in anhydrous methanol (1.5 L of), stirred and cooled to 5 . Was slowly added dropwise thionyl chloride (103.6g, 0.87mol), the dropwise addition was stirred at reflux for 6h. Cooling to room temperature, the reaction solution was concentrated under reduced pressure, the residue was diluted with ice water (1.2 L of), plus 5percent of NaHCO3 neutralized to pH7.5. The aqueous layer with ethyl acetate (3 × 600mL) extraction, the organic layer was mixed (2 × 500mL) and washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give a white solid intermediate (11) 62.7 g, yield 94.9percent.
94.9% at 5℃; for 6 h; Reflux 3-amino-4-methylbenzoic acid (60.5 g, 0.40 mol) was dissolved in anhydrous methanol (1.5 L), and the resultingsolution was cooled to 5°C with stirring. Thionyl chloride (103.6 g, 0.87 mol) was slowly added dropwise, and the reactionmixture was stirred under reflux for 6 h after the addition. After cooled to room temperature, the reaction mixture wasconcentrated under reduced pressure, and the residue was diluted with ice water (1.2 L), followed by neutralization topH 7.5 by adding 5percent NaHCO3. The aqueous layer was extracted with ethyl acetate (33600 mL), and the combinedorganic layer was washed with saturated brine (23500 mL), dried over anhydrous sodium sulfate, and filtered. Thefiltrate was concentrated under reduced pressure to obtain intermediate (11) as a white solid (62.7 g, yield: 94.9percent).MP 114-116°C1 H NMR (400 MHz, CDCl3): 2.19 (s, 3H), 3.73 (br s, 2H), 3.87 (s, 3H), 7.09 (m, 1H), 7.34-7.37 (m, 2H).
Reference: [1] Patent: CN105693520, 2016, A, . Location in patent: Paragraph 0184; 0185; 0186; 0187; 0188; 0189
[2] Patent: EP3067351, 2016, A1, . Location in patent: Paragraph 0083; 0084
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 14, p. 6724 - 6731
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2423 - 2435
  • 15
  • [ 2458-12-0 ]
  • [ 82998-57-0 ]
Reference: [1] Chemische Berichte, 1893, vol. 26, p. 1733
  • 16
  • [ 2458-12-0 ]
  • [ 5162-82-3 ]
  • [ 82998-57-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 5, p. 1333 - 1337
  • 17
  • [ 2458-12-0 ]
  • [ 7356-52-7 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 44, p. 8735 - 8746
[2] Patent: WO2015/27222, 2015, A2,
[3] Patent: WO2018/218070, 2018, A2,
  • 18
  • [ 2458-12-0 ]
  • [ 37901-90-9 ]
Reference: [1] Patent: WO2015/27222, 2015, A2,
[2] Patent: WO2018/218070, 2018, A2,
  • 19
  • [ 2458-12-0 ]
  • [ 60710-80-7 ]
Reference: [1] Patent: CN104557357, 2018, B,
  • 20
  • [ 64-17-5 ]
  • [ 2458-12-0 ]
  • [ 41191-92-8 ]
Reference: [1] European Journal of Inorganic Chemistry, 2006, # 5, p. 980 - 987
[2] Chemical Biology and Drug Design, 2014, vol. 83, # 5, p. 592 - 599
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4731 - 4739
  • 21
  • [ 2458-12-0 ]
  • [ 745048-63-9 ]
YieldReaction ConditionsOperation in experiment
89% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 1.16667 h; Inert atmosphere To a solution of acid 24 (81 g, 535.8 mmol) in DMF (500 mL) was added NBS portionwise at 0 °C. The mixture was stirred at 0 °C for 70 min. The mixture was poured into H2O (1 L) with stirring. The product was precipitated and filtered. The solid was washed with H2O and the solid was dried under vacuum at 50 °C for 24 h to obtain the bromide (109 g, 89percent)To a solution of bromide (109 g, 473.8 mmol) in MeOH (900 mL) was added thionyl chloride (70 mL, 947.6 mmol) dropwise at 0 °C. The mixture was warmed up to r.t. and stirred at 65 °C for 18 h. The mixture was evaporated in vacuo. The residue was diluted with EtOAc (500 mL) and washed with aq. sat'd NaHCO3 solution (700 mL.x.3). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo to obtain the ester 25 (107 g, 92percent).To a solution of ester 25 (60.4 g, 229 mmol) in CCl4 (900 mL) were added NBS (49.0 g, 275 mmol) and AIBN (3.80 g, 22.9 mmol). The mixture was stirred at 85 °C for 15 h. The mixture was cooled to room temperature and filtered off through celite to remove insoluble solids. The filtrate was evaporated in vacuo to obtain the crude benzyl bromide.To a solution of benzyl bromide (93.6 g, 273 mmol) in DMF (500 mL) was added NaOAc (56 g, 683 mmol). The mixture was stirred at room temperature for 20 h and diluted with EtOAc. The organic layer was washed with aq. 50percent NaCl solution and dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was tritulated with MeOH and the titled compound was precipitated as a solid. The solid was filtered off, washed with MeOH, and dried under vacuum to obtain the product (36 g, 51percent, 2 steps). 1H NMR (400 MHz, CDCl3) δ 7.84 (s, 1H), 7.71 (s, 2H), 5.19 (s, 2H), 3.94 (s, 3H), 2.19 (s, 3H); MH+ 321.To a solution of acetate (33.5 g, 104.1 mmol) in THF/MeOH/H2O (250 mL/250 mL/90 mL) was added lithium hydroxide monohydrate (13.1 g, 312 mmol). The mixture was stirred at room temperature for 15 h. The mixture was evaporated in vacuo to remove organic solvents. The residue was diluted with H2O, cooled to 0 °C and acidified with aq. 1 N HCl solution. The titled compound 26 was precipitated as a solid, filtered off and washed with H2O. The solid was dried under vacuum at 50 °C for 15 h to obtain the product (27.2 g, 96percent). MH+ 265.
89% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 1 h; Inert atmosphere the bromination at the 6-position of 3-amino-4-methylbenzoic acid 23 using NBS yields bromide 24 in 89percent yield
87% With N-Bromosuccinimide In N,N-dimethyl-formamide at 5 - 15℃; for 1 h; To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (412.2 g, 2.72 mole) in DMF (2.2 L) was added N-bromosuccinimide (495.1 g, 2.78 mole) in small portions at such a rate that the reaction mixture temperature was kept below 15° C.
After being stirred for one hour, the reaction mixture was poured onto ice water (1.2 L) with stirring.
The solid that formed was filtered, and the filter cake was washed with ice water (3*2 L) and then dried at 60° C. to give a pink solid. Yield: 546 g (87percent).
1H NMR (DMSO-d6, 300 MHz): δ 7.20 (s, 1H), 7.04 (s, 1H), 2.05 (s, 3H).
87% With N-Bromosuccinimide In N,N-dimethyl-formamide at 5 - 15℃; for 1 h; To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (412.2 g, 2.72 mole) in DMF (2.2 L) was added N-bromosuccinimide (495.1 g, 2.78 mole) in small portions at such a rate that the reaction mixture temperature was kept below 15° C.
After being stirred for one hour, the reaction mixture was poured onto ice water (1.2 L) with stirring.
The solid that formed was filtered, and the filter cake was washed with ice water (3*2 L) and then dried at 60° C. to give a pink solid. Yield: 546 g (87percent).
1H-NMR (DMSO-d6, 300 MHz): δ 7.20 (s, 1H), 7.04 (s, 1H), 2.05 (s, 3H).
85% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 15℃; for 2 h; Inert atmosphere 5-Amino-2-bromo-4-methylbenzoic acid[0116] 3-amino-4-methylbenzoic acid (24.72 g, 162 mmol) was dissolved in anhydrous DMF (140 mL). The solution was then cooled to 0 - 5ºC and N-bromosuccinimide (29.70 g, 163.5 mmol) was added portionwise at a rate that the reaction mixture was kept below 15 ºC. The mixture was reacted for 2 hours and then poured into ice/water (150 g) with stirring. The produced solid was filtered and washed with cool water (3 x 120 mL). The filter cake was dissolved with EtOAc (800 mL) and washed with water (3 × 200 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to afford 5-amino-2-bromo-4-methylbenzoic acid as a pink solid (31.59 g, 85percent yield).
85% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 15℃; for 2 h; Inert atmosphere In a round-bottom flask equipped with magnetic stirring and inert atmosphere, 3- amino-4-methylbenzoic acid (24.72 g, 162 mmol) was dissolved in anhydrous DMF (140 mL). The solution was then cooled to 0 - 5^C and /V-bromosuccinimide (29.70 g, 163.5 mmol) was added portionwise at a rate that the reaction mixture was kept below 15 2C. The mixture was reacted for 2 hours and then poured into ice/water (150 g) with stirring. The produced solid was filtered and washed with cool water (3 x 120 mL). The filter cake was dissolved with EtOAc (800 mL) and washed with water (3 x 200 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to dryness under vacuum to afford 5-amino-2-bromo-4-methylbenzoic acid as a pink solid (31.59 g, 85percent yield).
83% With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 20℃; for 3 h; Example 14
Preparation of 3-Amino-6-bromo-4-methylbenzoic Acid (19)
A mixture of 3-amino-4-methylbenzoic acid (13) ((13) (5.1525 g, 34.08 mmol)) and DMF (30 ML) is cooled to about 5° C., whereupon N-bromosuccinimide (6.230 g, 35 mmol) is added in small portions, at a rate such that the reaction temperature stays below 10° C.
The reaction mixture is then stirred at ambient temperature for about 3 hours and is then added to ice water (150 ML).The solids that form are filtered and dried to provide 3-Amino-6-bromo-4-methylbenzoic Acid (19) ((19) (6.5439 g, 83percent yield).
77.5% With N-Bromosuccinimide In N,N-dimethyl-formamide at 15℃; for 1 h; Step 1:
Preparation of 5-amino-2-bromo-4-methylbenzoic acid
To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (3.02 g, 20 mmol) in DMF (20 mL) was added NBS (3.38 g, 19 mmol) in small portions at such a rate that the reaction mixture temperature was kept below 15° C.
After being stirred for one hour, the reaction mixture was poured onto ice water (100 mL) with stirring.
The solid formed was collected by filtration, and the filter cake was washed with ice water (3*100 mL) and then dried at 60° C. under high vacuum to give 5-amino-2-bromo-4-methylbenzoic acid (3.55 g, yield 77.5percent) as a pink solid. MS: m/z=230.0 (M+1, ESI+).

Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 7, p. 2662 - 2675
[2] Patent: WO2011/159067, 2011, A2, . Location in patent: Page/Page column 28
[3] Patent: US2007/275907, 2007, A1, . Location in patent: Page/Page column 19
[4] Patent: US2008/242596, 2008, A1, . Location in patent: Page/Page column 15
[5] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 19, p. 5632 - 5635
[6] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6877 - 6881
[7] ChemMedChem, 2010, vol. 5, # 6, p. 827 - 831
[8] Patent: EP2573088, 2013, A1, . Location in patent: Paragraph 0116; 0117
[9] Patent: WO2013/45495, 2013, A1, . Location in patent: Page/Page column 41
[10] Patent: US2004/167194, 2004, A1, . Location in patent: Page 26
[11] Patent: US2013/131017, 2013, A1, . Location in patent: Paragraph 0380; 0581
[12] Chinese Chemical Letters, 2013, vol. 24, # 2, p. 131 - 133
[13] Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1715 - 1721
  • 22
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  • [ 170487-40-8 ]
Reference: [1] Patent: CN105693520, 2016, A,
[2] Patent: EP3067351, 2016, A1,
  • 23
  • [ 24424-99-5 ]
  • [ 2458-12-0 ]
  • [ 231958-04-6 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In water at 20℃; for 18 h; To a solution of 3-amino-4-methyl benzoic acid (2.0 g, 13.2 mmol) in water (25 mL) and 1N sodium hydroxide (25 mL) was added di-tert-butyl dicarbonate (4.3 g, 19.8 mmol) and the reaction was stirred for 18 hours at ambient temperature. The reaction was partitioned between ethyl acetate and 5percent aqueous citric acid. The organic layer was washed with water and brine and dried over magnesium sulfate. The material was filtered and concentrated to provide the protected aniline as a pink solid (3.3 g, quantitative yield).
91% at 50℃; A mixture of commercially-available 4-amino-3-methylbenzoic acid (100 g, 0.66 mol) and di-tertbutyl dicarbonate (150 g, 0.68 mol) in THF (1000 mL) was slowly heated to 50°C overnight. The resulting mixture was cooled to rt and the solvent was removed on a rotary evaporator. The resulting solids were triturated with hexanes and dried in vacuo to afford 151 g (91percent) of the crude BOC-protected aniline intermediate as a light pink solid. To the above, light-pink solid was added 1- (3- dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (127 g, 0.66 mol), HOBt (90 g, 0.66 mol), and DMF (1000 ml), and the resulting mixture was stirred at rt for 30 minutes followed by addition of methoxyamine hydrochloride (55 g, 0.66 mol) in one portion. After stirring for 10 min, the mixture was cooled using an ice bath. Diisopropyl-ethylamine (250 ml, 1.4 mol) was added at such a rate so as to maintain the internal reaction temperature below 25°C. After the addition was complete, the ice bath was removed and the reaction was stirred overnight at rt. The reaction mixture was partitioned between 0.5 L of water and 1.5 L of EtOAc and the resulting layers were separated. The aqueous portion was extracted with additional EtOAc (400 mL x 3), and the combined organic extracts were washed with, water (300 mL x 3), cold 0.5 N aqueous HC1 (400 mL x 2), and water (500 mL). The product was then extracted with cold 0.5 N aqueous NaOH (300 mL x 3) and the combined basic aqueous extracts were neutralized to pH = 8 by a slow addition of cold 0.5 N aqueous HC1. The resulting solid which precipitated was collected by filtration and washed with cold water.'The wet solid was decolorized in hot EtOH with active charcoal to give 106 g of white solid as the BOC-protected N-methoxyamide intermediate. To a slurry of the above solid (91 g, 0.32 mol) in 1,4-dioxane (400 mL) at rt was added a 4M solution of HC1 in dioxane (400 mL), and the resulting mixture was stirred at rt overnight. Diethyl ether (1000 mL) was added and the precipitated solid was collected by filtration and triturated with a hot EtOH/H20 mixture (4: 1 v/v). Drying the resulting solid in vacuo afforded 53 g of the pure hydrochloride salt (1D) as a white solid. 1H NMR (d6-DMSO) : 6 9.5-9. 9 (br. s, 1H), 7.75 (s, 1H), 7.55 (d, 1H), 7.36 (d, 1H), 3.70 (s, 3H), 2.38 (s, 3H).
88% at 50℃; A suspension of 3-amino-4-methylbenzoic acid (20.0 g, 132 mmol) and N-(tert-butoxycarbonyl)anhydride (30.0 g, 219 mmol) in THF (200 mL) was heated and stirred at 50 °C overnight. The resulting mixture was cooled to rt. The solvent was evaporated in vacuo, and the crude product was recrystallized from EtOAc to afford 7 (29.1 g, 88 percent) as a pink solid. 1H NMR (DMSO-d6): δ 12.8 (s, 1H), 8.66 (s, 1H), 7.97 (s, 1H), 7.59 (dd, J=2.0, 8.0Hz, 1H), 7.28 (d, J=8.0Hz, 1H), 3.25 (s, 3H), 1.47 (s, 9H).
Reference: [1] Patent: US2012/142708, 2012, A1, . Location in patent: Page/Page column 23
[2] Patent: WO2005/42537, 2005, A1, . Location in patent: Page/Page column 46; 47
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 3700 - 3705
[4] European Journal of Organic Chemistry, 2001, # 2, p. 311 - 322
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 1, p. 4 - 16
[6] Angewandte Chemie - International Edition, 2017, vol. 56, # 47, p. 14918 - 14922[7] Angew. Chem., 2017, vol. 129, # 47, p. 15114 - 15118,5
  • 24
  • [ 2458-12-0 ]
  • [ 641569-94-0 ]
Reference: [1] Chemical Biology and Drug Design, 2014, vol. 83, # 5, p. 592 - 599
  • 25
  • [ 2458-12-0 ]
  • [ 474330-54-6 ]
Reference: [1] Patent: WO2011/159067, 2011, A2,
[2] Patent: EP2573088, 2013, A1,
[3] Patent: WO2013/45495, 2013, A1,
[4] Chinese Chemical Letters, 2013, vol. 24, # 2, p. 131 - 133
[5] Monatshefte fur Chemie, 2015, vol. 146, # 10, p. 1715 - 1721
[6] Patent: US2013/131017, 2013, A1,
  • 26
  • [ 2458-12-0 ]
  • [ 641569-96-2 ]
Reference: [1] Chemical Biology and Drug Design, 2014, vol. 83, # 5, p. 592 - 599
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