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[ CAS No. 97240-79-4 ] {[proInfo.proName]}

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Chemical Structure| 97240-79-4
Chemical Structure| 97240-79-4
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Product Details of [ 97240-79-4 ]

CAS No. :97240-79-4 MDL No. :MFCD00865320
Formula : C12H21NO8S Boiling Point : -
Linear Structure Formula :- InChI Key :KJADKKWYZYXHBB-XBWDGYHZSA-N
M.W : 339.36 Pubchem ID :5284627
Synonyms :
McN 4853;RWJ 17021;Topax;Tipiramato;HSDB-7531;TPM

Calculated chemistry of [ 97240-79-4 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 9.0
Num. H-bond donors : 1.0
Molar Refractivity : 71.75
TPSA : 123.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : -0.83
Log Po/w (WLOGP) : 0.69
Log Po/w (MLOGP) : -0.65
Log Po/w (SILICOS-IT) : -0.91
Consensus Log Po/w : 0.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.22
Solubility : 20.3 mg/ml ; 0.0598 mol/l
Class : Very soluble
Log S (Ali) : -1.29
Solubility : 17.3 mg/ml ; 0.051 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.02
Solubility : 32.6 mg/ml ; 0.0959 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.94

Safety of [ 97240-79-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335-H351-H361 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 97240-79-4 ]

* 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 [ 97240-79-4 ]

[ 97240-79-4 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 150609-95-3 ]
  • [ 97240-79-4 ]
YieldReaction ConditionsOperation in experiment
91.1% With pyridine; SULFAMIDE In 5,5-dimethyl-1,3-cyclohexadiene at 128 - 133℃; for 3 h; 30 g of fructose diacetone, 28 ml of pyridine, 12.5 g of sulfonamide were added at room temperature, and then slowly heated to 128-133 ° CReaction for 3 hours. Natural cooling to 40 , adding MIBK100ml, add water 48ml stirring down to 20 by adding 50percent sodium hydroxide solution 18.5g stirring for 30 minutes, the organic phase separation. 54 ml of purified water was added to the aqueous phase, and the combined aqueous phase was distilled off under reduced pressure by 30 ml. Down to room temperature with hydrochloric acid to adjust pH6-7, cooling to 0-5 stirring crystallization 2 hours, filter, filter cake with a small amount of purified water, the resulting solid 60 below drying. The crude product 31 g was obtained in a yield of 79.3percent.The crude product obtained was heated to 55 ° C with 35 ml of 95percent ethanol and dissolved by adding 0.5 g of activated charcoal.Crystallized at 10 ° C for 2 hours, filtered and dried at 50 ° C or below to obtain topiramate 28 g in a yield of 90.3percent and a liquid phase purity of 98.54percent. The procedure was repeated twice with 32 ml of 95percent ethanol to give topiramate 25.5 g yield 91.1percent and liquid phase purity 99.15percent.
90% With ammonia In ethanol at 20℃; for 6 h; Green chemistry; Industrial scale (2) The reaction product obtained in the step (1) is dissolved in 1000 L of ethanol, and 15 kg of ammonia gas is introduced under stirring, and stirring is continued for 6 hours at room temperature.The reactant is heated and refluxed to dissolve, and then slowly cooled and crystallized. And stirred at 10 ° C for 4 h, centrifuged, and the filter cake was washed with ethanol several times; 3) The reaction product obtained in the step (2) is heated to reflux to dissolve under a pressure of 15 times by volume of the reaction product of cyclohexane.Slowly reduce the temperature to 65 °C, add 0.5kg of topiramate seed crystal with a purity of more than 99percent, continue to slowly cool down to 5 °C for 6h, and centrifuge.The filter cake was washed with low temperature cyclohexane and dried to obtain 135 kg of topiramate, the mass yield was 90.0percent, the purity of HPLC was 99.7percent, and the maximum single impurity was <0.07percent.
67% With ammonia; pyrographite In 1,2-dichloro-ethane at 25℃; for 10 - 12 h; Into the same 20 L 4-necked round bottom flask, ethylene dichloride (10 L) was added to the oily product of Step I containing 2,3:4,5-bis-O-(1-methylethylidene)-β-fructopyranose sulfonyl chloride (about 11 L). Charcoal (120 g) dispersed in ethylene dichloride (200 ml) was added at a temperature of about 25° C. under stirring. Dry ammonia gas was bubbled through the reaction mixture at a temperature of about 25° C. under stirring for between 10 to 12 hours. After completion of the reaction as determined by TLC, the mixture was filtered through a Hyflow bed and washed with ethylene dichloride (500 ml). All the washings were then collected. The ethylene dichloride layer was concentrated on a rotavapor at a temperature of about 65° C. under reduced pressure until no more drops were observed. The oil (about 1.25 kg) after distillation was dissolved in isopropanol (1.2 L) and ethyl acetate (0.6 L) and filtered through a Hyflow bed. The isopropanol and ethyl acetate solution was added to n-hexane (3.6 L) under stirring and maintained for about 1 hour at 25° C. The solution was cooled to a temperature of about 0° C. and maintained for about 1 hour under stirring. The precipitated solid was filtered and dried in a vacuum oven at a temperature of about 55° C. until the loss on drying reached below 1percent. The product appears as an off-white to pale yellow solid. Net wt=about 975 g, yield=about 75percent, purity of about 97-98percent. The product was dissolved in isopropanol (1.2 L) and ethyl acetate (0.6 L) and filtered through a Hyflow bed. The isopropanol and ethyl acetate solution was added to n-hexane (3.6 L) under stirring and maintained for about 1 hour at a temperature of about 25° C. The solution was cooled to a temperature of about 0° C. and maintained for about 1 hour under stirring. The dried solid appears as a white crystalline solid. Net wt=about 875 g, yield=about 67percent, purity of >99.5percent, mp 122-124° C., specific rotation [α]D 20=-33 (c=0.4percent in MeOH). IR (KBr) spectrum shows absorption bands 3385 cm-1 (-N-H str), 3100 (-C-H str), 1390, 1186 cm-1 (-SO2str). 1H-NMR spectrum (CDCl3, TMS as internal standard) shows δ 1.35, 1.40, 1.45, 1.55 (4S,12H,CH3), 3.8 (m,2H,H6), 4.1-4.4(m,4H), 4.5-4.7 (dd,1H4), 5.2 (br,2 NH2). Mass: m/z 340 (M+).
67% With ammonia In 1,2-dichloro-ethane at 20 - 25℃; for 10 - 12 h; Into the same 4-necked round bottom flask, ethylene dichloride (10 volumes with respect to 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfonyl chloride) was added to the oily product of Step I containing 2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfonyl chloride. Dry ammonia gas was bubbled through the reaction mixture at a temperature of about 20-25° C. under stirring for between 10 to 12 hours. After completion of the reaction as determined by TLC, charcoal was added to the reaction mixture (10percent w/w with respect to. starting material), stirred the reaction mixture for 1.0 hour, filtered through a Hyflow bed and washed with ethylene dichloride (2 volumes with respect to starting material). All the washings were then collected. The ethylene dichloride layer was concentrated on a rotavapor at a temperature below 50° C. under reduced pressure and degas for 30 minutes. The oil after distillation was dissolved in isopropanol (one volume with respect to starting material) and ethyl acetate (0.5 volume with respect to starting material) and heat the reaction mass to 50-55° C. to get the clear solution. To the isopropanol and ethyl acetate solution, n-hexane (4.5 volumes with respect to starting material) was added under stirring for about one hour and cooled the reaction mixture to 25-30° C. in 2 hours. The solution was cooled to a temperature of about 0-5° C. and maintained for about 2 hour under stirring. The precipitated solid was filtered and dried in a vacuum oven at a temperature of about 55° C. until the loss on drying reached below 1percent. The product appeared as an off-white to pale yellow solid. Net wt=about 975 g, yield=about 75percent, and purity of about 97-98percent. The product was dissolved in isopropanol and ethyl acetate and filtered through a Hyflow bed. The reaction mixture was heated to 50-55° C. to provide a clear solution. The n-hexane was added slowly to isopropanol and ethyl acetate solution under stirring and maintained for about 1 hour at a temperature of about 25° C. The solution was cooled to a temperature of about 0-5° C. and maintained for about 1 hour under stirring. The precipitated solid was filtered, washed with 0.5 volumes of n-hexane (with respect to crude topiramate) and then dried for 1.0 hour. Next, the dried product was dissolved in isopropanol and heated to 60 to 70° C. Water was added slowly to the isopropanol solution. The solution was cooled to a temperature of about 5-10° C. and maintained for about 2 hour under stirring. The precipitated solid was filtered and dried in a vacuum oven at a temperature of about 50-55° C. until the loss on drying reached below 1percent. Yield=about 67percent, purity of >99.5percent, mp 122-124° C., specific rotation [α]D 20=-33 (c=0.4percent in MeOH). IR (KBr) spectrum shows absorption bands 3385 cm-1 (-N-H str), 3100 (-C-H str), 1390, 1186 cm-1 (-SO2str). 1H-NMR spectrum (CDCl3, TMS as internal standard) shows δ 1.35, 1.40, 1.45, 1.55 (4S,12H,CH3), 3.8 (m,2H,H6), 4.1-4.4(m,4H), 4.5-4.7 (dd,1H4), 5.2 (br,2 NH2). Mass: m/z 340 (M+).
225.37 g With ammonium acetate In tetrahydrofuran; acetonitrile at 60℃; for 4 h; A solution of 2,3: 4,5-bis -O- (1- methylethylidene) -β-D- fructopyranose chlorosulfonic acid ester (350g, 0.978mol) was dissolved with stirring in tetrahydrofuran ( 3000mL) and acetonitrile (300mL), followed by addition of ammonium acetate (226g, 2.934mol), heated to 60 , the reaction was stirred for 4 hours.The reaction was cooled to room temperature, filtered, the filtrate was concentrated under reduced pressure to give the crude product as a pale yellow solid.Topiramate crude product with n-hexane (1200mL) - ethanol (400mL) recrystallization, filtration, and dried to yield topiramate 225.37g, HPLC purity greater than 99percent.The first product was recrystallized from n-hexane: ethanol mixed solvent volume ratio of 3:1 again recrystallized to give topiramate 202.17g

Reference: [1] Patent: CN106632530, 2017, A, . Location in patent: Paragraph 0012; 0071; 0072
[2] Patent: CN108341844, 2018, A, . Location in patent: Paragraph 0023; 0026; 0027; 0028; 0031; 0032; 0033; 0036
[3] Patent: EP1627881, 2006, A1, . Location in patent: Page/Page column 3
[4] Patent: US2005/203287, 2005, A1, . Location in patent: Page/Page column 5
[5] Patent: US2005/203287, 2005, A1, . Location in patent: Page/Page column 6
[6] Patent: WO2004/41836, 2004, A1, . Location in patent: Page 30-33; 35-38; 39-40; 41
[7] Patent: WO2004/108732, 2004, A1, . Location in patent: Page 9; 10
[8] Patent: WO2011/96934, 2011, A1, . Location in patent: Page/Page column 12
[9] Patent: CN105566405, 2016, A, . Location in patent: Paragraph 0027; 0028; 0029
[10] Patent: CN106397502, 2017, A, . Location in patent: Paragraph 0021-0022; 0024-0027; 0029-0032; 0034-0035
  • 2
  • [ 20880-92-6 ]
  • [ 97240-79-4 ]
YieldReaction ConditionsOperation in experiment
76% With 4-methyl-morpholine; sulphamoyl chloride In di-isopropyl ether; N,N-dimethyl-formamide at 5℃; for 1 h; Crude product recrystalization EXAMPLE 3The procedure of example 1 was followed with 100 ml dimethylformamide instead of dimethyl acetamide.Water content (by Karl Fisher) = 0.13percent; Chemical assay (by HPLC) = 99.0percent; Yield = 76percent (by theory)
75% With sulphamoyl chloride; triethylamine In di-isopropyl ether; N,N-dimethyl acetamide at 5℃; for 1 h; Crude product recrystalization EXAMPLE 2The procedure of example 1 was followed with 26 gm of triethylamine instead of N- methylmorpholine .Water content (by Karl Fisher) = 0.17percent; Chemical assay (by HPLC) = 99.1percent; Yield = 75percent (by theory)
72% With 4-methyl-morpholine; sulphamoyl chloride In di-isopropyl ether; N,N-dimethyl acetamide at 5 - 10℃; for 1 h; Crude product recrystalization EXAMPLE 1Topiramate crude2,3:4,5-bis-O-(l-methylethylidene)-?-D-fructopyranose (50 gm) (III) and N- methylmorpholine (26 gm) were suspended in 100 ml dimethyl acetamide. The mass was cooled to 50C followed by addition of 29.8 gm of sulfamoyl chloride (V). The reaction mass was stirred at that temperature for 1 hr and extracted with 250 ml ethyl acetate followed by further extraction with 2 x 100 ml ethyl acetate. The organic layer was washed with 400 ml water and 200 ml 20percent sodium chloride solution and concentrated in vacuum to a mass. This was then crystallized with a mixture of 75 ml ethyl acetate and 150 ml cyclohexane. The crystalline product was filtered and dried at 550C under vacuum to get 50 gm of Topiramate crude.Topiramate pure50 gm of the above crude was dissolved in 2200 ml diisopropyl ether at reflux temperature till a clear solution was obtained. Activated carbon (2.5 gm) was added and the contents were refluxed for another 30 min followed by filtration under hot conditions. The filtrate was concentrated till a residual volume of 250 ml was achieved. The crystallized product was cooled to 100C and filtered. The product was dried at 500C under vacuum to get 45 gm of Topiramate pure.Water content (by Karl Fisher) = 0.15percent; Chemical assay (by HPLC) = 99.2percent; Yield = 77percent (by theory)EXAMPLE 4The procedure of example 1 was followed with the change that the reaction temperature was maintained at 100C instead of 5C.Water content (by Karl Fisher) = 0.17percent; Chemical assay (by HPLC) = 99.3percent; Yield = 72percent (by theory)
Reference: [1] Patent: WO2007/99388, 2007, A1, . Location in patent: Page/Page column 6
[2] Patent: WO2007/99388, 2007, A1, . Location in patent: Page/Page column 5-6
[3] Patent: WO2007/99388, 2007, A1, . Location in patent: Page/Page column 5; 6
[4] Journal of Medicinal Chemistry, 1987, vol. 30, # 5, p. 880 - 887
[5] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 6; 13; 46
[6] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[7] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[8] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[9] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[10] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[11] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 31; 33
[12] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 31; 33-34
[13] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 31; 33-34
[14] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 31; 33-34
[15] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[16] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[17] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[18] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 28; 32-33
[19] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 19; 21; 22-23; 28; 32-33
[20] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 32-33
[21] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 28; 32-33
[22] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 16-18; 22
[23] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22
[24] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[25] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 29; 32; 34
[26] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32-33
[27] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 16-25; 29; 32; 34-38; 39-41
[28] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32-33
[29] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32; 34
[30] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27-28; 32-34
[31] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32; 34
[32] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 29; 32; 34
[33] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[34] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 28; 32; 34
[35] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[36] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 29; 32; 34
[37] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 16-18; 22; 29; 32; 34
[38] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 41-42
[39] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22; 27; 32-33; 39-41
[40] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[41] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[42] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[43] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 21; 23; 25-26
[44] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 32; 34
[45] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 32; 34
[46] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 32; 34
[47] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[48] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 17; 20; 22
[49] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 30; 33-34
[50] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[51] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 27; 33-34
[52] Patent: WO2004/78769, 2004, A1, . Location in patent: Page 37-38
[53] Journal of Sulfur Chemistry, 2015, vol. 36, # 5, p. 463 - 470
[54] Patent: CN103910770, 2017, B,
  • 3
  • [ 106881-35-0 ]
  • [ 97240-79-4 ]
Reference: [1] Patent: WO2004/89965, 2004, A2, . Location in patent: Page title page; 9-10
  • 4
  • [ 876403-98-4 ]
  • [ 97240-79-4 ]
YieldReaction ConditionsOperation in experiment
61%
Stage #1: With sodium hydroxide; water; acetic acid In acetone at 78 - 79℃; for 1 - 8.5 h; Heating / reflux
Stage #2: With sodium hydroxide In water; acetone
The N-(diethylamino)carbonyl derivative prepared according to Example 1.2 (5 g) is dissolved in a mixture of acetone (12 ml), acetic add (11 ml) and water (12.5 ml) and the pH is adjusted to 2.5 by 1 M sodium hydroxide (0.4 ml). The resulting solution is heated to reflux at 78-79° C. After 1 hour TLC shows the consumption of the starting material. The cooled mixture is neutralised with 10 M sodium hydroxide and extracted with methylene chloride (4.x.15 ml). The collected organic phases are dried on magnesium sulphate and concentrated to obtain the crude product as syrup (5.5 g). It is then crystallised from 2-propanol (4 ml) and water (14.5 ml) to give white crystals. Yield is 2.95 g. HPLC (area percent): 99.8; Further examples are presented in Table 1 TABLE 1 Time Yield HPLC Example pH hour percent area percent 2.2.1 3.0 1.5 83.2 99.8; 2.2.2 3.5 1 72 99.6; 2.2.3 4.0 3 69 99.7; 2.2.4 4.5 3 61 99.6; 2.2.5 5.0 8.5 77 99.1
61% With sodium hydroxide; acetic acid In water; acetone at 78 - 79℃; for 1 - 8.5 h; Heating / reflux The N-(diethylamino)carbonyl derivative prepared according to Example 1.2 (5 g) is dissolved in a mixture of acetone (12 ml), acetic acid (11 ml) and water (12.5 ml) and the pH is adjusted to 2.5 by 1 M sodium hydroxide (0.4 ml). The resulting solution is heated to reflux at 78-79° C. After 1 hour TLC shows the consumption of the starting material. The cooled mixture is neutralised with 10 M sodium hydroxide and extracted with methylene chloride (4 x 15 ml). The collected organic phases are dried on magnesium sulphate and concentrated to obtain the crude product as syrup (5.5 g). It is then crystallised from 2-propanol (4 ml) and water (14.5 ml) to give white crystals. Yield is 2.95 g HPLC (areapercent): 99.8 Further examples are presented in Table 1 Table 1 Example pH Time hour Yield percent HPLC areapercent 2.2.1 3.0 1.5 83.2 99.8 2.2.2 3.5 1 72 99.6 2.2.3 4.0 3 69 99.7 2.2.4 4.5 3 61 99.6 2.2.5 5.0 8.5 77 99.1
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[2] Patent: EP1627881, 2006, A1, . Location in patent: Page/Page column 10
[3] Patent: US2006/40874, 2006, A1, . Location in patent: Page/Page column 7
[4] Patent: US2006/40874, 2006, A1, . Location in patent: Page/Page column 7
[5] Patent: EP1627881, 2006, A1, . Location in patent: Page/Page column 11
[6] Patent: EP1627881, 2006, A1, . Location in patent: Page/Page column 11
  • 5
  • [ 627538-01-6 ]
  • [ 97240-79-4 ]
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  • 6
  • [ 106881-41-8 ]
  • [ 122-51-0 ]
  • [ 433-27-2 ]
  • [ 97240-79-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 8, p. 1315 - 1343
  • 7
  • [ 57-48-7 ]
  • [ 97240-79-4 ]
Reference: [1] Journal of Sulfur Chemistry, 2015, vol. 36, # 5, p. 463 - 470
  • 8
  • [ 7660-25-5 ]
  • [ 97240-79-4 ]
Reference: [1] Patent: CN108341844, 2018, A,
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