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Quality Control of [ 139481-44-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 139481-44-0 ]

SDS Specification

Alternatived Products of [ 139481-44-0 ]

Product Details of [ 139481-44-0 ]

CAS No. :	139481-44-0	MDL No. :	MFCD09031384
Formula :	C₂₅H₂₁N₃O₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	KSXLHOFDCDKQLH-UHFFFAOYSA-N
M.W :	411.45	Pubchem ID :	15654674
Synonyms :

Calculated chemistry of [ 139481-44-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	31
Num. arom. heavy atoms :	21
Fraction Csp3 :	0.16
Num. rotatable bonds :	7
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	118.21
TPSA :	77.14 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.89
Log Po/w (XLOGP3) :	4.9
Log Po/w (WLOGP) :	4.81
Log Po/w (MLOGP) :	3.34
Log Po/w (SILICOS-IT) :	4.83
Consensus Log Po/w :	4.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-5.52
Solubility :	0.00125 mg/ml ; 0.00000304 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.26
Solubility :	0.000228 mg/ml ; 0.000000555 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.13
Solubility :	0.00000304 mg/ml ; 0.0000000074 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.28

Safety of [ 139481-44-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 139481-44-0 ]

* 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 [ 139481-44-0 ]

[ 139481-44-0 ] Synthesis Path-Downstream 1~10

1
[ 78-09-1 ]
[ 136304-78-4 ]
[ 139481-44-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With acetic acid; at 80℃; for 1h;	To a solution of compound 8 in tetraethyl orthocarbonate (5 mL), acetic acid (0.37 g) was added, and the mixture was stirred at 80 °C for 1 h, the reaction mixture was concentrated, and the residue was dissolved in ethyl acetate. Washed with water, evaporated to dryness, The crystal was recrystallized from ethyl acetate-hexane.Obtained 2.01g of colorless crystal,Yield 86percent, compound 5.
84.8%	With acetic acid; at 78 - 82℃; for 1 - 2h;Heating / reflux; Industry scale;	The concentrate of methyl 3-amino-2-N-[(2'-cyanobiphenyl-4-yl)methyl]aminobenzoate [MBA] obtained in Reference Example5, tetraethyl orthocarbonate [TEC] obtained in Reference Example 6 (397 kg) and acetic acid (62 kg) were mixed, and the mixture was heated (78 to 82°C) under reflux for about 1 to 2 hrs.. The reaction solution was cooled, and methanol (1680 L), a 24percent aqueous sodium hydroxide solution (65 L) and water (2030 L) were added.. The mixture was stirred at 60 to 30°C for 2 hours, and the PH was adjusted to 5 to 7.. After cooled to 5°C or lower, the precipitated crystals were separated, and washed with cold water (2500 L) and cold ethyl acetate (500 L) to give first crystals.. The mother liquor and the washing were concentrated under reduced pressure, followed by cooling to 5°C or lower, and the precipitated crystals were separated, and washed with cold ethyl acetate (20 L) to give second crystals.. The first and second crystals were combined, and dissolved in ethyl acetate (4890 L) under reflux.. A seed crystal was added at about 70°C, and cooled to 5 °C. The crystals were separated, and washed with cold ethyl acetate (200 L), followed by drying to give methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate [BEC](361 kg, 84.8percent). mp. 168.5-169.5°C 1H-NMR(200MHz, CDCl3) delta: 1.42(3H,t), 3.71(3H,s), 4.63(2H,q), 5.59(2H,s), 7.09(2H,d), 7.20(1H,t), 7.45-7.59(5H,m), 7.69-7.80(2H,m), 7.92(1H,dd) IR(KBr) cm-1: 2225, 1725, 1550, 1480, 1430, 1280, 1250, 1040, 760, 750
	With acetic acid; In toluene; at 20℃;Reflux;	Example 1; To the solution of Methyl-3-amino-2-[[2'-cyanobiphenyl-4-yl]methyl]amino] benzoate (100 gm) in toluene (500 ml), tetraethyl ortho carbonate (125 gm) and acetic acid (20 gm) were added at room temperature and refluxed for 6 hours.Distilled off toluene under vacuum below 600C, added methanol (300 ml) at 550C, stirred for 20 minutes, cooled to room temperature, filtered and then washed with methanol (90 ml). Dried for 6 hours to yield Methyl-1-[(2-cyano biphenyl-4- yl)methyl]-2-ethoxy benzimidazole-7-carboxylate (90 gm, HPLC purity: 98.9percent).

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2182 - 2195
[2]Patent: CN108658961,2018,A .Location in patent: Paragraph 0011; 0062; 0064
[3]Patent: EP1420016,2004,A1 .Location in patent: Page 18-19
[4]Patent: WO2009/157001,2009,A2 .Location in patent: Page/Page column 3

2
[ 139481-44-0 ]
[ 139481-69-9 ]

Yield	Reaction Conditions	Operation in experiment
85%		Preparation of 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- lH-benzimidazole-7-carboxylic acid methyl ester To 2-ethoxy-1-[[2'-cyano [l, 1'-biphenyl] -4-yl] methyl]-lH-benzimidazole-7- carboxylic acid methyl ester of Formula IV (310 g) in toluene (2.48 L) added tributyltin chloride (737 g) and sodium azide (146 g) and tetrabutyl ammonium bromide (31 g). The resultant mass was slowly heated to 110°C and maintained for 24 hours at 110-115°C. The reaction was monitored by TLC and after completion of reaction, the reaction mass was cooled to 15°C. Added methanol (3.1 L) and water (2.17 L) to the reaction mass followed by addition of acetic acid (930 g). The resultant mixture was stirred at 15-20°C for 1 hour to allow separation of the product. Charged toluene (1.24 L) at 15-20°C and filtered the reaction mass. Washed the cake thoroughly with water (0.93 L) to completely remove the acidity (until the pH of the washing is between about 5.5 to about 7.0). Washed the cake with toluene (0.62 L) and suck dried. Air dried the product at 50-55°C to afford the title compound. Yield: 290 g (85percent)
		Compound I, 1-(2'-cyanobiphenyl-4-yl)methyl)-2-ethoxybenzimidazole-7-carboxylic acid methyl ester (111 g, 270 mmol), is reacted in an aromatic hydrocarbon, preferably toluene, xylolene or mesitylene (typically, 500-1000 mL), with alkali metal azides and another reagent (ammonium halide derivatives, typically, triethylamine hydrochloride or organotin halides, typically, tetramethyltin chloride or tetrabutyltin chloride), while heating, to form compound II, 2-ethoxy-1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)benzimidazole-7-carboxylic acid methyl ester. After completion of the reaction, the reaction solution is stirred with water or a saline solution (250 mL), whereupon the solids dissolve and a three-phase liquid system forms. If only two phases are present, petroleum spirit 80/110 is added until there are three phases which can be separated well. The lower phase is separated; the two upper phases are washed with water or a saline solution (200 mL).
	With tri-n-octyltin azide; In toluene; at 112 - 120℃; for 40h;Heating / reflux; Industry scale;	The methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]2-ethoxybenzimidazole-7-carboxylate [BEC] (228 kg) obtained in Reference Example 7, the concentrate of trioctyltin azide [TOTA] obtained in Reference Example 8 and toluene (1148 L) were heated (115 to 120°C) under reflux for about 40 hours. The reaction solution was cooled, and concentrated under reduced pressure. Ethanol (764 kg) and an aqueous sodium nitrite solution (135 kg/460 L) were added to the residue, and the pH was adjusted to 4.5 to 5.5 with concentrated hydrochloric acid (about 224 kg). Ethyl acetate (735 L) was added thereto, and the pH was adjusted to 0.5 to 1.5 with concentrated hydrochloric acid (about 100 L). Hexane (1005 L) was added, and the pH was adjusted to 3.5 +/- 0.5 with 4percent aqueous sodium hydroxide solution. The solution was cooled to 10°C or lower, and stirred for 1 hour. The crystals were separated, and washed with a mixture of ethyl acetate (106 L) and hexane (310 L), and then with hexane (410 L) to give wet MET (396.6 kg).

	With sodium azide; tributyltin chloride; In toluene; for 100h;Reflux;	To sodium azide (48 gm) was added water (500 ml), cooled to O0C, tributyl tin chloride (240 gm) was added, maintained for 2 hours 30 minutes, added toluene (500 ml) and then allowed the temperature to rise to room temperature. Separated the layers, re-extracted using toluene (500 ml) and organic layer washed with 10percent sodium chloride solution (480 ml). Methyl-1-[(2- cyanobiphenyI-4-yl)methyl]-2-ethoxy benzimidazole-7-carboxylate (100 gm) was added to above solution, refluxed for 100 hours, cooled to room temperature and then to 100C. Methanol (400 ml), water (300),and acetic acid (320 ml) were added at O0C. Stirred for 8 hours at room temperature, then cooled to O0C, stirred for 3 hours, filtered, washed with toluene (400 ml) and dried the solid at 600C to get Methyl-2-ethoxy-1-[[2'-(1 H-tetrazole-5-yl)biphenyl-4-yl]methyl] benzimidazole- 7-carboxylate (80 gm, HPLC purity: 96percent).
		To 75.0 grams of <strong>[139481-44-0]methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate</strong> were added 375 ml xylene and 2.5 moles of tri-n-butyltin azide, which was prepared with sodium azide and tri-n-butyltin chloride inthe presence of water and extracted with methylene chloride. The mixture wasslowly heated to reflux and maintained for 24 hours, and then the solvent wasevaporated under reduced pressure. The residue was dissolved in 225 ml ofmethanol and 225 ml of water followed by the addition of 91.3 grams of sodiumnitrite and 75 ml of ethyl acetate. The pH of the resulting solution was adjusted to3 with aqueous hydrochloric acid. The upper liquid layer was decanted and 225ml of ethyl acetate was added. The solid was filtered, washed with ethyl acetate,and dried at 50-60°C to get 82.0 grams (98percent) of methyl 2-ethoxy-1-[[2'-(1 H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate.
	With azido tributyltin (IV); In N,N-dimethyl-formamide; at 140 - 150℃; for 20h;	Trityl candesartan was prepared from candesartan cyclic compound in the similar manner as Example 1. The results are shown in the following table.

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2182 - 2195
[2]Patent: WO2005/51929,2005,A1 .Location in patent: Page/Page column 18
[3]Patent: US2009/203920,2009,A1 .Location in patent: Page/Page column 4
[4]Patent: EP1420016,2004,A1 .Location in patent: Page 19
[5]Patent: WO2009/157001,2009,A2 .Location in patent: Page/Page column 3
[6]Patent: WO2006/15134,2006,A1 .Location in patent: Page/Page column 16-17
[7]Patent: US2018/155326,2018,A1 .Location in patent: Paragraph 0035

3
[ 139481-44-0 ]
[ 147403-65-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In N,N-dimethyl acetamide; water; at 70℃; for 18h;	N, N-dimethylacetamide 2L,Water 16L, added to the reaction bottle,Hydroxylamine hydrochloride (3.37 kg 48.6 mol) was added,Sodium carbonate (5.15 kg 48.6 mol) was added,<strong>[139481-44-0]1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylic acid methyl ester</strong>(2 kg, 4.86 mol)70 ° C for 18 hours,Cooling, adding water 2L,Precipitation of solid,Filtration was 2-ethoxy-1-[2'-(N'-hydroxycarbamimidoyl)biphenyl-4-yl]-1H-benzimidazole-7-carboxylic acid methyl ester (1.94 g, 37.70 mol),Reference is made to Examples1HPLC conditions Purity: 98.9percent Yield: 90percent.
85%	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In dimethyl sulfoxide; at 80 - 85℃; for 20h;	Dimethyl sulfoxide (75 mL) and hydroxylamine hydrochloride (6 g) were stirred at 20°C to 30°C. Sodium bicarbonate (9 g) was added to the solution and stirred at 45 °C to 50 °C for 1 hour. Methyl-1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (3 g) was added to the reaction mixture and heated at 80 °C to 85 °C for 20 hours. The reaction mixture was cooled to 20 °C to 30 °C and de-ionized water (75 mL) was added to the reaction mixture. The solid obtained was filtered and washed with water (75 mL). The solid obtained was purified in 2-butanol (15 mL) at 90 °C to 95 °C for 4 hours and further cooled to 20 °C to 30 °C for 4 hours. The solid obtained was filtered, washed with 2-butanol (6 mL), and dried to obtain the title compound. Yield: 2.75 g (85percent) HPLC Purity: 96.89percent
75%	With hydroxylamine hydrochloride; sodium carbonate; In N,N-dimethyl-formamide; at 60℃; for 24h;	60 g of N,N-dimethylformamide was added to the reaction flask.Add 19.5 g of sodium carbonate with stirring and mix well.Add 8.5 g of hydroxylamine hydrochloride and warm to 35 ° C.The reaction was stirred for 30 minutes and 25 g of compound IV-1 was added.Continue to raise the temperature to 60 ° C, stir the reaction for 24 h, after the reaction is over,The crystallized crystals were cooled and filtered to obtain a crude compound III-1. The crude product obtained,DMSO was added to the reaction flask, and the temperature was crystallized for 1 hour, and the temperature was crystallized.Filtration and drying gave Compound III-1 in a yield of 75percent.

70.4%	With hydroxylamine hydrochloride; sodium carbonate; In dimethyl sulfoxide; at 90℃;	To a 500 mL four-neck flask, 20 g of Compound 1 was added, and while stirring, 100 mL of dimethyl sulfoxide solution in which 10.14 g (3 eq) of hydroxylamine hydrochloride was added was added, and the mixture was heated to 90 DEG C and 30.95 g (6 eq) was added in portions under stirring. Sodium carbonate, after the completion of the reaction for 9-10 hours, after the completion of the reaction, it is allowed to come to room temperature, and 100 mL of water is added to stir the mixture. The solid precipitates, which is cooled down to 0-5°C. Stirring is continued for about 1 hour, and the mixture is dried by suction to obtain 15.2 g of compound 2. The yield was 70.4percent.
35%	With hydroxylamine hydrochloride; triethylamine; In dimethyl sulfoxide; at 20 - 75℃; for 6h;	Weighed hydroxylamine hydrochloride (60.8mmol), triethylamine (63.2mmol), dimethyl sulfoxide 60mL was added to a 100mL two-neck round bottom flask, stirred at room temperature for 30min, added to the reaction system1-[(2'-Cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylic acid methyl ester (6.08 mmol) was reacted at 75 ° C for 6 h and the reaction was completed. Thereafter, the mixture was cooled to room temperature, and the product in the reaction mixture was extracted with dichloromethane, distilled under reduced pressure, solvent was removed, and recrystallized to give 1-[(2'-(hydroxyindolyl)[1,1-biphenyl]- Methyl 4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate, yield 35percent.
	With hydroxylamine hydrochloride; sodium hydrogencarbonate; In dimethyl sulfoxide; at 25 - 90℃; for 18h;	Example 1Preparation of methyl 2-ethoxy [[2'-(hydroxyamidino) biphenyl-4-yl] methyI]-lH- benzimidazole-7-carboxylateTo a solution of hydroxylamine hydrochloride (122 g) and dimethylsulfoxide (1000 ml), Sodium bicarbonate (204 g) was added at 25-30°C, which was further heated to 45-50°C. To the resulting solution l-[(2'cyanobiphenyl-4-yl)methyl]-2-ethoxy benzimidazole-7-carboxylate (40 g) was added and the resulting solution was heated to 85-90°C followed by stirring at the same temperature for about 18 h. Reaction mass was cooled to 15-20°C. Water was added and the solution was stirred for 15-20 min at 15- 20°C. The product was filtered, washed and dried to obtain title compound. (Yield: 38 g; 88percent; (Purity: 87percent with amide impurity 3.86percent.
55 g	With hydroxylamine hydrochloride; sodium hydroxide; In methanol; N,N-dimethyl acetamide; at 10 - 75℃; for 0.5h;Inert atmosphere;	Methanol (400 mL) and sodium hydroxide (56.44 g) were added under a nitrogen atmosphere and stirred at 20° C. to 30° C. to get a clear solution. Dimethylacetamide (750 mL) and hydroxylamine hydrochloride (101.45 g) were added under a nitrogen atmosphere and stirred at 20° C. to 30° C. to get clear solution. Methanolic sodium hydroxide solution was added to the solution of hydroxylamine hydrochloride in dimethylacetamide at 25° C. to 30° C. The reaction mixture was stirred for 30 minutes. Methyl-1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate (100 g) was added to the reaction mixture at 25° C. to 30° C. and heated to 70° C. to 75° C. for 16 hours to 20 hours. The reaction mixture was cooled to 10° C. to 15° C. The reaction mixture was added to deionized water (1000 mL) at 10° C. to 25° C. The pH of the reaction mixture was adjusted to 0.8 to 1.2 using concentrated hydrochloric acid (150 mL). The reaction mixture was stirred for 30 minutes at 20° C. to 30° C. The reaction mixture was filtered through celite and washed with deionized water (100 mL). The aqueous layer was washed with toluene (500 mL) at 25° C. to 30° C. and the pH of the aqueous layer was adjusted to 8.8 to 9.2 using 30percent solution of sodium carbonate (500 mL) at 20° C. to 30° C. The reaction mixture was stirred for 3 hours to 4 hours at 25° C. to 30° C. The reaction mixture was filtered and washed with deionized water (100 mL) at 20° C. to 30° C. Isobutanol (500 mL) was added to the reaction mixture at 20° C. to 30° C. and the reaction mixture was heated to 90° C. to 95° C. The reaction mixture was stirred for 2 hours at 90° C. to 95° C., cooled to 25° C. to 30° C., and stirred for 4 to 6 hours at 25° C. to 30° C. The reaction mixture was filtered and washed with isobutanol (100 mL) at 20° C. to 30° C. The reaction mixture was dried under vacuum for 30 minutes at 20° C. to 30° C. and then at 45° C. to 50° C. to obtain the title compound. Yield: 55 g
191.3g	With hydroxylamine hydrochloride; sodium hydrogencarbonate; sodium sulfite; In dimethyl sulfoxide; at 50 - 85℃; for 12h;	Taking anhydrous sodium sulfite 122.5 g (0.972 mol)Sodium bicarbonate 408.4 g (4.861 mol)Was added to 2.4 L of DMSO, stirred,A mixture of hydroxylamine hydrochloride (270.2 g, 3.889 mol)Temperature control 50 ~ 55 stirring reaction 2h,Was added 1 - [(2 - cyanobiphenyl-4-yl) methyl] -2-ethoxy-benzimidazole-7-carboxylate (200g, 0.486mol),Temperature control 80 ~ 85 stirring reaction 10h,Rapid dropwise addition of 2.4L water stirring crystallization,Temperature control 20 ~ 25 stirring for 1h,Filtration to give compound II191.3g.HPLC was used to detect compound II 99.07percent and amide impurity 0.32percent.
	With tetrabutyl-ammonium chloride; hydroxylamine; triethylamine; In ethanol; water; for 30h;Reflux;	Add 1000g to the 20L reaction bottleMethyl 2-ethoxy-1-((2'-cyanobiphenyl-4-yl)methyl)-1H-benzimidazole-7-carboxylate (II),1473 mL of 50percent aqueous hydroxylamine solution, 340 mL of triethylamine, 1 g of sodium hexametaphosphate, 0.5 g of tetrabutylammonium chloride and 8 L of industrial ethanol (95percent ethanol). The reaction solution was heated to reflux for 30 h, slightly cooled, and filtered while hot. After cooling and crystallization for 8 h, the solid obtained by suction filtration was dried at 45 ° C for 8 h to obtain white solid intermediate III 910 g, yield: 91.5percent, purity 91.7percent.

Reference： [1]Patent: CN103408500,2016,B .Location in patent: Paragraph 0026; 0046-0047
[2]Patent: WO2013/114305,2013,A1 .Location in patent: Page/Page column 15; 16
[3]Organic Process Research and Development,2015,vol. 19,p. 514 - 519
[4]Organic Process Research and Development,2013,vol. 17,p. 77 - 86
[5]Patent: CN108912109,2018,A .Location in patent: Paragraph 0091
[6]Patent: CN103242305,2018,B .Location in patent: Paragraph 0038-0040
[7]Journal of Medicinal Chemistry,1996,vol. 39,p. 5228 - 5235
[8]Patent: CN108752328,2018,A .Location in patent: Paragraph 0033; 0035; 0036
[9]Patent: WO2012/107814,2012,A1 .Location in patent: Page/Page column 13
[10]Patent: US2015/11774,2015,A1 .Location in patent: Paragraph 0052; 0053
[11]Patent: CN106478515,2017,A .Location in patent: Paragraph 0025; 0026; 0027; 0028; 0029; 0030; 0031-0038
[12]Patent: CN108456202,2018,A .Location in patent: Paragraph 0026; 0028; 0030; 0032; 0034; 0036-0038; 0042

4
[ 139481-44-0 ]
[ 147403-03-0 ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 5228 - 5235
[2]Patent: WO2012/107814,2012,A1
[3]Organic Process Research and Development,2013,vol. 17,p. 77 - 86
[4]Organic Process Research and Development,2013,vol. 17,p. 77 - 86
[5]Organic Process Research and Development,2013,vol. 17,p. 77 - 86
[6]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 929 - 936
[7]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 929 - 936
[8]Journal of Heterocyclic Chemistry,2013,vol. 50,p. 929 - 936
[9]Patent: CN103408500,2016,B
[10]Patent: CN103664920,2016,B
[11]Patent: CN103242305,2018,B
[12]Patent: CN108752328,2018,A
[13]Patent: CN108947993,2018,A
[14]Patent: CN108947993,2018,A

5
[ 139481-44-0 ]
2-Ethoxy-3-[2'-(5-oxo-4,5-dihydro-[1,2,4]thiadiazol-3-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid [ No CAS ]