合成路线1
该中间体在本合成路线中的序号:
(IX) The reaction of cyclopentanone (I) with sodium cyanide, NH3 and NH4Cl in hot methanol/water gives 1-aminocyclopentanecarbonitrile (II), which is partially hydrolyzed with concentrated H2SO4 to the corresponding amide (III). The acylation of (III) with pentanoyl chloride (IV) by means of triethylamine in THF yields 1-(pentanamido)cyclopentane-1-carboxamide (V), which, without isolation, is cyclized by means of KOH in refluxing methanol/water to afford 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one (VI). This compound (VI) can also be obtained by cyclization of 1-aminocyclopentanecarboxylic acid ethyl ester (VII) with pentanimidic ethyl ester (VIII) by means of acetic acid in refluxing xylene. The condensation of (VI) with 4'-(bromomethyl)biphenyl-2-carbonitrile (IX) by means of NaH in DMF gives 4'-(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-ylmethyl)biphenyl-2-carbonitrile (X). Cyclization of (X) with tributyltin azide in refluxing xylene, followed by reaction with trityl chloride in DMF, affords 2-butyl-3-[2'-[1-(triphenylmethyl)tetrazol-5-yl]biphenyl-4-ylmethyl]-1,3-diazaspiro[4.4]non-1-en-4-one (XI). Finally, this compound is hydrolyzed to irbesartan with HCl in methanol/THF. The final cyclization of (X) with tributyltin azide or sodium azide also directly gives irbesartan.
【1】
Casas, A.; Merlos, M.; Castaner, J.; Irbesartan. Drugs Fut 1997, 22, 5, 481.
|
【2】
Bernhart, C.; Breliere, J.-C.; Clement, J.; Nisato, D.; Perreaut, P. (Sanofi-Synthélabo ); Heterocyclic N-substd. derivs., their preparation and the pharmaceutical compsns. containing them. EP 0454511; FR 2659967; FR 2665702; JP 1992506222; JP 1998279566; US 5270317; WO 9114679 . |
【3】
Caron, A.; Chantreux, D.; Bouloumie, C. (Sanofi-Synthelabo ); Method for the preparation of a tetrazole deriv. under two crystalline forms and novel crystalline form of this deriv. EP 0708103 .
|
【4】
Bernhart, C.A.; Perreaut, P.M.; Ferrari, B.P.; et al.; A new series of imidazolones: Highly specific and potent nonpeptide AT1 angiotensin II receptor antagonists. J Med Chem 1993, 36, 22, 3371-80.
|
【5】
Bernhart, C.; Clement, J.; Ferrari, B.; et al.; Spiro-dihydro-imidazolones, a new class of non-peptide angiotensin II receptor antagonists. 12th Int Symp Med Chem (Sept 13-17, Basel) 1992, Abst P-084.A..
|
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(I) |
15113 |
cyclopentanone
|
120-92-3 |
C5H8O |
详情 | 详情
|
(II) |
15114 |
1-aminocyclopentanecarbonitrile
|
|
C6H10N2 |
详情 |
详情
|
(III) |
15115 |
1-Amino-1-cyclopentane carboxamide; 1-Aminocyclopentanecarboxamide
|
17193-28-1 |
C6H12N2O |
详情 | 详情
|
(IV) |
15116 |
pentanoyl chloride; valeryl chloride
|
638-29-9 |
C5H9ClO |
详情 | 详情
|
(V) |
15117 |
N-[1-(aminocarbonyl)cyclopentyl]pentanamide; 1-(pentanoylamino)cyclopentanecarboxamide
|
|
C11H20N2O2 |
详情 |
详情
|
(VI) |
15118 |
2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one; 1,3-Diazaspirol[4,4]non-1-en-4-one,2-butyl
|
151257-01-1 |
C11H18N2O |
详情 | 详情
|
(VII) |
15119 |
ethyl 1-aminocyclopentanecarboxylate
|
|
C8H15NO2 |
详情 |
详情
|
(VIII) |
15120 |
ethyl pentanimidoate
|
|
C7H15NO |
详情 |
详情
|
(IX) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(X) |
15122 |
4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl][1,1'-biphenyl]-2-carbonitrile
|
|
C25H27N3O |
详情 |
详情
|
(XI) |
15121 |
2-butyl-3-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one
|
|
C44H42N6O |
详情 |
详情
|
合成路线2
该中间体在本合成路线中的序号:
(V) This compound can be obtained by two related ways:
1) The partial esterification of 3-nitrophthalic acid (I) with ethanol and H2SO4 gives 3-nitrophthalic acid 1-monoethyl ester (II), which is treated with SOCl2 in refluxing benzene to yield the corresponding acyl chloride (III). The reaction of (III) first with sodium azide in DMF and then with refluxing tert-butanol affords 2-(tert-butoxycarbonylamino)-3-nitrobenzoic acid ethyl ester (IV), which is condensed with 4-(2-cyanophenyl)benzyl bromide (V) by means of NaH in THF giving 2-(2'-cyanobiphenyl-4-ylmethylamino)-3-nitrobenzoic acid ethyl ester (VI). The reduction of (VI) with SnCl2.2H2O in ethanol yields the corresponding 3-amino derivative (VII), which is cyclocondensed with ethyl orthocarbonate and acetic acid affording 1-(2'-cyanobiphenyl-4-ylmethyl)-2-ethoxybenzimidazole-7-carboxylic acid ethyl ester (VIII). The reaction of (VIII) with trimethyltin azide in refluxing toluene gives the 2'-(1H-tetrazol-5-yl) derivative (IX), which is saponified with NaOH in ethanol to the corresponding free acid (X). Protection of (X) with trityl chloride and triethylamine in dichloromethane gives the protected compound (XI), which is finally esterified with cyclohexyl 1-iodoethyl carbonate (XII) by means of K2CO3 in DMF.
2) Compound (VIII) can also be obtained by reaction of 2-chloro-1-(2'-cyanobiphenyl-4-ylmethyl)benzimidazole-7-carboxylic acid ethyl ester (XIII) with sodium ethoxide in refluxing ethanol.
【1】
Naka, T.; Nishikawa, K.; Kato, T. (Takeda Chemical Industries, Ltd.); Benzimidazole derivs., their production and use. EP 0459136; EP 0720982; JP 1992364171; JP 1996099960; US 5196444; US 5328919; US 5401764; US 5703110; US 5705517; US 5962491; US 6004989 . |
【2】
Prous, J.; Mealy, N.; Castaner, J.; TCV-116. Drugs Fut 1993, 18, 7, 609.
|
【3】
Obara, Y.; Kubo, K.; Imamiya, E.; Sugiura, Y.; Inada, Y.; Shibaida, Y.; Ishikawa, K.; Yoshimura, Y.; Naka, T.; Synthesis of TCV-116, a new non-peptide angiontensin II (AII) receptor antagonist and its AII antagonist action. 113th Annu Meet Pharmaceut Soc Jpn (March 29-31, Osaka) 1993, Abst 29CC 13-5. |
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(I) |
15328 |
3-Nitrophthalic acid
|
603-11-2 |
C8H5NO6 |
详情 | 详情
|
(II) |
15329 |
2-(ethoxycarbonyl)-6-nitrobenzoic acid
|
|
C10H9NO6 |
详情 |
详情
|
(III) |
15330 |
ethyl 2-(chlorocarbonyl)-3-nitrobenzoate; 2-Ethoxycarbonyl-6-nitrobenzoyl chloride
|
|
C10H8ClNO5 |
详情 |
详情
|
(IV) |
15331 |
ethyl 2-[(tert-butoxycarbonyl)amino]-3-nitrobenzoate
|
|
C14H18N2O6 |
详情 |
详情
|
(V) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(VI) |
15333 |
ethyl 2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-nitrobenzoate
|
|
C23H19N3O4 |
详情 |
详情
|
(VII) |
15334 |
ethyl 3-amino-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]benzoate
|
136285-69-3 |
C23H21N3O2 |
详情 | 详情
|
(VIII) |
15335 |
ethyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate
|
|
C26H23N3O3 |
详情 |
详情
|
(IX) |
15336 |
ethyl 2-ethoxy-1-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylate
|
|
C26H24N6O3 |
详情 |
详情
|
(X) |
15337 |
2-ethoxy-1-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid
|
|
C24H20N6O3 |
详情 |
详情
|
(XI) |
15338 |
2-ethoxy-1-[[2'-(1-trityl-1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylic acid
|
139481-72-4 |
C43H34N6O3 |
详情 | 详情
|
(XII) |
15339 |
cyclohexyl 1-iodoethyl carbonate
|
102672-57-1 |
C9H15IO3 |
详情 | 详情
|
(XIII) |
15340 |
ethyl 2-chloro-1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-1H-benzimidazole-7-carboxylate
|
|
C24H18ClN3O2 |
详情 |
详情
|
合成路线3
该中间体在本合成路线中的序号:
(IX) 1) The cyclization of aniline (I) with propionylacetic acid methyl ester (II) by means of p-toluenesulfonic acid in refluxing cyclohexane gives 2-ethylquinolin-4(1H)-one (III), which is condensed with 5-[4'-(bromomethyl)biphenyl-2-yl]-2-(triphenylmethyl)tetrazole (IV) by means of NaH in DMF, yielding 2-ethyl-4-[2'-[1-(triphenylmethyl)tetrazol-5-yl]biphenyl-4-ylmethoxy] quinoline (V). Finally, this compound is deprotected with HCl in ethanol - methanol.
2) The condensation of 4-methylphenylboronic acid (VI) with 2-bromobenzonitrile (VII) by means of Na2CO3 and PdCl2 in toluene - methanol gives 2-(4-methylphenyl)benzonitrile (VIII), which is brominated with N-bromosuccinimide (NBS) and azobis(isobutyronitrile) (AIBN) in hot chlorobenzene, yielding the bromomethyl derivative (IX). The condensation of (IX) with quinolone (III) by means of K2CO3 in N-methylpyrrolidone affords 4-(2'-cyanobiphenyl-4-ylmethoxy)-2-ethylquinoline (X), which is treated with tributyltin hydrazide in refluxing toluene to afford 2-ethyl-4-[2'-[2-(tributyltin)tetrazol-5-yl]biphenyl-4-ylmethoxy] quinoline (XI). Finally, this compound is deprotected with NaNO2 and HCl in cool water.
【1】
Roberts, D.A.; Russell, S.T.; Pearce, R.J. (AstraZeneca plc); Quinoline derivs., process for their preparation and their use as medicaments. AU 9160955; EP 0412848; GB 2234748; JP 1991169863; US 5444071 .
|
【2】
Prous, J.; Castaner, J.; Graul, A.; ICI-D8731. Drugs Fut 1993, 18, 5, 428.
|
【3】
Bradbury, R.H.; Allott, C.P.; Dennis, M.; et al.; New nonpeptide angiotensin II receptor antagonists. 2. Synthesis, biological properties, and structure-activity relationships of 2-alkyl-4-(biphenylylmethoxy)quinoline derivatives. J Med Chem 1992, 35, 22, 4027. |
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(I) |
12294 |
Aniline; Phenylamine
|
62-53-3 |
C6H7N |
详情 | 详情
|
(II) |
15536 |
methyl 3-oxopentanoate
|
30414-53-0 |
C6H10O3 |
详情 | 详情
|
(III) |
15537 |
2-ethyl-4(1H)-quinolinone
|
|
C11H11NO |
详情 |
详情
|
(IV) |
15538 |
5-[4'-(bromomethyl)[1,1'-biphenyl]-2-yl]-2-trityl-2H-1,2,3,4-tetraazole
|
124750-51-2 |
C33H25BrN4 |
详情 | 详情
|
(V) |
15539 |
2-ethyl-4-quinolinyl [2'-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl ether; 2-ethyl-4-[[2'-(2-trityl-2H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methoxy]quinoline
|
|
C44H35N5O |
详情 |
详情
|
(VI) |
15540 |
4-methylphenylboronic acid; p-Tolylboronic acid
|
5720-05-8 |
C7H9BO2 |
详情 | 详情
|
(VII) |
15541 |
o-bromobenzonitrile; 2-bromobenzonitrile
|
2042-37-7 |
C7H4BrN |
详情 | 详情
|
(VIII) |
13929 |
2-Cyano-4'-methylbiphenyl; 4'-Methyl[1,1'-biphenyl]-2-carbonitrile
|
114772-53-1 |
C14H11N |
详情 | 详情
|
(IX) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(X) |
15544 |
4'-[[(2-ethyl-4-quinolinyl)oxy]methyl][1,1'-biphenyl]-2-carbonitrile
|
|
C25H20N2O |
详情 |
详情
|
(XI) |
15545 |
5-[4'-(2-Ethylquinolin-4-yloxymethyl)biphenyl-2-yl]-2-(tributylstannyl)-2H-tetrazole
|
|
C37H47N5OSn |
详情 |
详情
|
合成路线4
该中间体在本合成路线中的序号:
(I) This compound has been obtained by two related ways:
1) The hydrolysis of 4'-(bromomethyl)biphenyl-2-carbonitrile (I) with NaOAc in refluxing acetic acid gives the corresponding carbinol (II), which is oxidized with oxalyl chloride in DMSO/dichloromethane yielding the aldehyde (III). The reductocondensation of (III) with L-valine methyl ester (IV) by means of NaBH4CN in THF affords the N-alkylated valine (V), which is acylated with pentanoyl chloride (VI) and TEA in dichloromethane providing the pentanamide (VII). The reaction of the CN group of (VII) with tributyltin azide in refluxing xylene gives the tetrazol derivative (VIII). Finally, the ester group of (VIII) is hydrolyzed with NaOH to furnish the target compound.
2) L-valine methyl ester (IV) can be condensed directly with the bromo-methyl derivative (I) by means of DIEA in dichloromethane giving the N-alkylated valine (V) already reported.
【1】
Buhlmayer, P.; Ostermayer, F.; Schmidlin, T. (Novartis AG); Acyl cpds.. EP 0443983; JP 1992235149; US 5399578; US 5965592 .
|
【2】
Buhlmayer, P.; et al.; Valsartan, a potent, orally active angiotensin II antagonist developed from the structurally new amino acid series. Bioorg Med Chem Lett 1994, 4, 1, 29.
|
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(I) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(II) |
37265 |
4'-(hydroxymethyl)[1,1'-biphenyl]-2-carbonitrile
|
|
C14H11NO |
详情 |
详情
|
(III) |
37266 |
4'-formyl[1,1'-biphenyl]-2-carbonitrile
|
|
C14H9NO |
详情 |
详情
|
(IV) |
16613 |
methyl (2S)-2-amino-3-methylbutanoate
|
|
C6H13NO2 |
详情 |
详情
|
(V) |
37267 |
methyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate
|
|
C20H22N2O2 |
详情 |
详情
|
(VI) |
15116 |
pentanoyl chloride; valeryl chloride
|
638-29-9 |
C5H9ClO |
详情 | 详情
|
(VII) |
37268 |
methyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl](pentanoyl)amino]-3-methylbutanoate
|
|
C25H30N2O3 |
详情 |
详情
|
(VIII) |
37269 |
methyl (2S)-3-methyl-2-(pentanoyl[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amino)butanoate
|
|
C25H31N5O3 |
详情 |
详情
|
合成路线5
该中间体在本合成路线中的序号:
(III) The reaction of 2-bromo-4'-methylbiphenyl (I) with 14C labeled cuprous cyanide in refluxing DMF gives 4'-methylbiphenyl-2-carbonitrile (II), which is brominated with NBS and AIBN in refluxing CCl4 to yield the bromomethyl derivative (III). The condensation of (III) with L-valine benzyl ester (IV) by means of DIEA in hot DMF affords the N-substituted valine (V), which is acylated with pentanoyl chloride (VI) and DIEA to provide the N-acylated valine (VII). The cyclization of the cyano group of (VII) with tributyltin azide at 140 C furnishes the tetrazol derivative (VIII) which is finally debenzylated by hydrogenation with H2 over Pd/C in dioxane.
【1】
Moenius, T.; et al.; Carbon-14 labelling of Diovan(TM) in its valine-moiety. J Label Compd Radiopharm 2000, 43, 13, 1245.
|
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(I) |
41935 |
2-bromo-4'-methyl-1,1'-biphenyl
|
|
C13H11Br |
详情 |
详情
|
(II) |
13929 |
2-Cyano-4'-methylbiphenyl; 4'-Methyl[1,1'-biphenyl]-2-carbonitrile
|
114772-53-1 |
C14H11N |
详情 | 详情
|
(II) |
45264 |
4'-methyl[1,1'-biphenyl]-2-carbonitrile
|
|
C14H11N |
详情 |
详情
|
(III) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(III) |
45265 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile
|
|
C14H10BrN |
详情 |
详情
|
(IV) |
41936 |
benzyl (2S)-2-amino-3-methylbutanoate
|
|
C12H17NO2 |
详情 |
详情
|
(V) |
41937 |
benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate; N-[(2'-cyanobiphenyl-4-yl)methyl]-L-valine benzyl ester
|
137864-23-4 |
C26H26N2O2 |
详情 | 详情
|
(V) |
45266 |
benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]amino]-3-methylbutanoate
|
|
C26H26N2O2 |
详情 |
详情
|
(VI) |
15116 |
pentanoyl chloride; valeryl chloride
|
638-29-9 |
C5H9ClO |
详情 | 详情
|
(VII) |
41938 |
benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl](pentanoyl)amino]-3-methylbutanoate
|
|
C31H34N2O3 |
详情 |
详情
|
(VII) |
45267 |
benzyl (2S)-2-[[(2'-cyano[1,1'-biphenyl]-4-yl)methyl](pentanoyl)amino]-3-methylbutanoate
|
|
C31H34N2O3 |
详情 |
详情
|
(VIII) |
41939 |
benzyl (2S)-3-methyl-2-(pentanoyl[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amino)butanoate
|
|
C31H35N5O3 |
详情 |
详情
|
(VIII) |
45268 |
benzyl (2S)-3-methyl-2-(pentanoyl[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]amino)butanoate
|
|
C31H35N5O3 |
详情 |
详情
|
合成路线6
该中间体在本合成路线中的序号:
(XXI) 4) The condensation of 2,4-dimethylpyrido[2,3-d]pyrimidin-7(8H)-one (XX) with 4'-(bromomethyl)biphenyl-2-carbonitrile (XXI) by means of NaH in DMF gives 8-(2'-cyanobiphenyl-4-ylmethyl)-2,4-dimethylpyrido[2,3-d]pyrimidin-7(8H)-one (XIX), which is then cyclized with sodium azide in refluxing xylene to afford metabolite (IV).
【1】
Ellingboe, J.W.; Collini, M.D.; Quagliato, D.; Chen, J.; Antane, M.; Schmid, J.; Hartupee, D.; White, V.; Park, C.H.; Tanikella, T.; Bagli, J.F.; Metabolites of the angiotensin II antagonist tasosartan: The importance of a second acidic group. J Med Chem 1998, 41, 22, 4251. |
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(IV) |
26039 |
2,4-dimethyl-8-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]pyrido[2,3-d]pyrimidin-7(8H)-one
|
|
C23H19N7O |
详情 |
详情
|
(XX) |
26037 |
2,4-dimethylpyrido[2,3-d]pyrimidin-7(8H)-one
|
|
C9H9N3O |
详情 |
详情
|
(XXI) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(XXII) |
26038 |
4'-[[2,4-dimethyl-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl]methyl][1,1'-biphenyl]-2-carbonitrile
|
|
C23H18N4O |
详情 |
详情
|
合成路线7
该中间体在本合成路线中的序号:
(III)
【1】
Hedvati L.Pilarsky G, Shenkar-Garcia N.2006. Process for preparing olmesartan medoxomil at pH higher than 2.5.US 20060148870 |
【2】
Hedvati L,Pilarsky G-2006. Prooess for the preparation of olmesartan medoxomiL. W0 2006029056(本专利属于Teva Pharmaceutical Industries Ltd.Israeli Teva Phumaceuticals Usa Inc) |
中间体序号 |
中间体编号 |
品名 |
CAS号 |
分子式 |
供应商 |
用于合成 |
(I) |
16906 |
diethyl 2-propyl-1H-imidazole-4,5-dicarboxylate
|
|
C12H18N2O4 |
详情 |
详情
|
(II) |
16907 |
ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate
|
|
C12H20N2O3 |
详情 |
详情
|
(III) |
15332 |
4'-(bromomethyl)[1,1'-biphenyl]-2-carbonitrile; 4'-bromomethyl-2-cyanobiphenyl
|
114772-54-2 |
C14H10BrN |
详情 | 详情
|
(IV) |
16919 |
ethyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-4-(1-hydroxy-1-methylethyl)-2-propyl-1H-imidazole-5-carboxylate
|
|
C26H29N3O3 |
详情 |
详情
|
(V) |
16920 |
ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-(1H-1,2,3,4-tetraazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylate
|
|
C26H30N6O3 |
详情 |
详情
|
(VI) |
66557 |
1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid |
144689-24-7 |
C24H26N6O3 |
详情 | 详情
|