BILS-179 BS, -Drug Synthesis Database

【结构式】

【药物名称】BILS-179 BS

【化学名称】N-[N-[4-(2-Aminothiazol-4-yl)phenyl]carbamoylmethyl]-N-[1(S)-phenylethyl]pyridine-4-carboxamide

【CA登记号】193346-73-5

【分子式】C₂₅H₂₃N₅O₂S

【分子量】457.55836

【开发单位】Boehringer Ingelheim (Originator)

【药理作用】Anti-Herpes Simplex Virus Drugs, Anti-Herpes Virus Drugs, ANTIINFECTIVE THERAPY, Antiviral Drugs

合成路线1

The acylation of N-[4-(4-aminophenyl)-2-thiazolyl]carbamic acid tert-butyl ester (I) with bromoacetyl bromide (II) gives the bromoacetamide (III), which is then condensed with (S)-alpha-methylbenzylamine (IV) to yield the glycinamide derivative (V). The acylation of (V) with 4-pyridylcarbonyl chloride affords the protected precursor (VI), which is finally deprotected to provide the target BILS 179 BS.

参考文献中间体

【1】 Crute, J.J.; et al.; Herpes simplex virus helicase-primase inhibitors are active in animal models of human disease. Nat Med 2002, 8, 4, 386.
【2】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Thavonekham, B.; Grygon, C.A.; Crute, J.J. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Phenyl thiazole derivs. with anti-herpes virus properties. EP 0871619; JP 2000502702; US 6057451; WO 9724343 .
【3】 Hargrave, K.D.; Simoneau, B.; Faucher, A.-M.; Crute, J.J.; Thavonekham, B.; Grygon, C. (Boehringer Ingelheim (Canada) Ltd.; Boehringer Ingelheim Pharmaceuticals Inc.); Antiherpes virus cpds. and methods for their preparation and use. US 6288091 .

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)	54066	tert-butyl 4-(4-aminophenyl)-1,3-thiazol-2-ylcarbamate	n/a	C₁₄H₁₇N₃O₂S	详情	详情
(II)	14005	2-Bromoacetyl bromide; Bromoacetyl bromide	598-21-0	C₂H₂Br₂O	详情	详情
(III)	54067	tert-butyl 4-{4-[(2-bromoacetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₁₆H₁₈BrN₃O₃S	详情	详情
(IV)	20042	(1S)-1-phenyl-1-ethanamine; (1S)-1-phenylethylamine		C₈H₁₁N	详情	详情
(V)	54068	tert-butyl 4-{4-[(2-{[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₂₄H₂₈N₄O₃S	详情	详情
(VI)	27850	isonicotinoyl chloride	39178-35-3	C₆H₄ClNO	详情	详情
(VII)	54069	tert-butyl 4-{4-[(2-{isonicotinoyl[(1S)-1-phenylethyl]amino}acetyl)amino]phenyl}-1,3-thiazol-2-ylcarbamate	n/a	C₃₀H₃₁N₅O₄S	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)