CAS: 68367-52-2; Sorbinil

上下游产品

6-氟-苯并二氢吡喃-4-酮海因 (+/-)-Sorbinil 69684-83-9
4-Acetamido-2,3-Dihydro-6-Fluoro-4H-1-Benzopyran-4-Carboxylic Acid 103197-08-6
(S)-4-Amino-6-Fluoro-Chromane-4-Carboxylic Acid 103834-11-3
(S)-Methyl 4-Amino-6-Fluorochroman-4-Carboxylate 103197-13-3
Methyl (4S)-Amino-2,3-Dihydro-6-Fluoro-4H-1-Benzopyran-4-Carboxylate 103197-16-6
(S)-4-Cyano-2,3-Dihydro-6-Fluoro-4-<(S)-(1-Phenylethyl)Amino>-4H-1-Benzopyran 79791-46-1
(4S)-4-(Diphenylphosphorylamino)-6-Fluoro-2,3-Dihydrochromene-4-Carbonitrile 692754-62-4

📜3-(4-氟苯氧基)丙腈置于盐酸,甲酸,Ppa,碳酸氢铵体系中,用 乙醇,水 作为反应溶剂,化学反应 67.33H,反应生成 索比尼尔
参考文献:醛糖还原酶抑制剂山梨醇的合成,绝对构型和构象.
标题:醛糖还原酶抑制剂山梨醇的合成,绝对构型和构象.
摘要:醛糖还原酶抑制剂2,3-二氢-6-氟螺[4H-1-苯并吡喃-4,4'-咪唑烷]-2',5'-二酮被拆分为其对映体.sorbinil,S异构体,在体内外比相应的r异构体是更好的酶抑制剂.介绍了用于确定其绝对构型的山梨醇x射线数据.溶液中山梨醇的NMR研究表明,存在两个构象异构体,它们具有较低的能量转换障碍.
DOI:10.1021/jm00149A030

专利信息

专利号:US-4431828-A
优先权日:1982-11-10
标题 :Regeneration of 6-fluoro-4-chromanone from by-products in the synthesis of sorbinil
发明人：CUE JR BERKELEY W; HAMMEN PHILIP D; MASSETT STEPHEN S
权利人:PFIZER
摘要:6-Fluoro-4-chromanone, a sorbinil intermediate, is regenerated from enantiomeric and mixtures of enantiomeric and racemic compounds obtained as major by-products in the synthesis of sorbinil. The regenerated intermediate is useful in the synthesis of additional sorbinil.

专利号:US-4286098-A
优先权日:1980-03-28
标 题:Process for the preparation of chiral hydantoins
发明人：SARGES REINHARD
权利人:PFIZER
摘要:A novel process for the synthesis of chiral hydantoins of the structure ##STR1## wherein X is fluoro or chloro, from the corresponding 6-halo-4-chromanone of the structure ##STR2## is described. The compounds I are valuable in the treatment of certain chronic complications arising from diabetes mellitus. In addition the compound of the formula I wherein X is chloro possesses complementary hypoglycemic activity. n The process comprises the sequence of dehydrative coupling of the halochromanone (II) with S-(-)-alpha-methylbenzylamine to form the imine of structure ##STR3## addition of hydrogen cyanide to form the nitrile of structure ##STR4## condensation with chlorosulfonylisocyanate (or its equivalent) to form the alpha-methylbenzylhydantoin of structure ##STR5## and finally solvolysis of the latter to the chiral hydantoin of structure I.

专利号:US-4348526-A
优先权日:1980-03-28
标题:Intermediates in the preparation of chiral hydantoins
发明人：SARGES REINHARD
权利人:PFIZER
摘要:A novel process for the synthesis of chiral hydantoins of the structure ##STR1## wherein X is fluoro or chloro, from the corresponding 6-halo-4-chromanone of the structure ##STR2## is described. The compounds I are valuable in the treatment of certain chronic complications arising from diabetes mellitus. In addition the compound of the formula I wherein X is chloro possesses complementary hypoglycemic activity. n The process comprises the sequence of dehydrative coupling of the halochromanone (II) with S-(-)-alpha-methylbenzylamine to form the imine of structure ##STR3## addition of hydrogen cyanide to form the nitrile of structure ##STR4## condensation with chlorosulfonylisocyanate (or its equivalent) to form the alpha-methylbenzylhydantoin of structure ##STR5## and finally solvolysis of the latter to the chiral hydantoin of structure I.

专利号:US-4419521-A
优先权日:1981-11-12
标 题 :6-Halo-4-chromanamines useful as intermediates to make chiral hydantoins
发明人：SARGES REINHARD
权利人:PFIZER
摘要:A novel process for the synthesis of chiral hydantoins of the structure (I) wherein X is fluoro or chloro, from the corresponding 6-halo-4-chromanone of the structure (II) is described. The compounds I are valuable in the treatment of certain chronic complications arising from diabetes mellitus. In addition the compound of the formula I wherein X is chloro possesses complementary hypoglycemic activity. The process comprises the sequence of dehydrative coupling of the halochromanone (II) with S-(-)-alpha-methylbenzylamine to form the imine of structure (III) addition of hydrogen cyanide to form the nitrile of structure (IV) condensation with chlorosulfonylisocyanate (or its equivalent) to form the alpha-methylbenzylhydantoin of structure (V) and finally solvolysis of the latter to the chiral hydantoin of structure I.

专利号:US-4812406-A
优先权日:1984-09-17
标题 :Process for preparing optically active hydantoins
发明人：TAKAHASHI SATOMI; YAMADA YUKIO; UEDA YASUYOSHI; KATAYAMA YASUHIRO; SHIMADA YOSHIO; WATANABE KIYOSHI
权利人:KANEGAFUCHI CHEMICAL IND
摘要:A process for preparing optically active hydantoins having the general formula (II): (II) wherein R1 and R2, which are different from each other, are independently alkyl group, aralkyl group, aryl group, substituted alkyl group, substituted aralkyl group, or substituted aryl group, or R1 and R2 form an asymmetric cyclic compound, characterized in that one configuration of racemic N-carbamoyl- alpha -amino acid having the general formula (I): (I) wherein R1 and R2 are as above, is enzymatically converted into the corresponding hydantoins. The present invention provides a process for an optical resolution with a high efficiency which can be used for the synthesis of (S)-6-fluoro-spiro-[chroman-4,4'-imidazolidine]-2',5'-dione (USAN; Sorbinil), which is an optically active hydrantoins attracting public attention as a preventive or a remedy for the particular chronic symptoms of diabetes such as cataract and neuropathy, and (S)- alpha -methyl-3,4-dihydroxyphenylalanine (L-methyldopa), which is an optically active amino acid widely used as antihypertensives. Further, the present invention provides a novel finding that N-carbamoyl- alpha -amino acid having no hydrogen atom on its alpha -carbon atom can be biochemically converted into hydantoins by an enzymatic cyclization reaction.

专利号:US-4625042-A
优先权日:1984-07-09
标 题 :Process for preparing 6-fluoro-4-chromanone using 3-(4-fluorophenoxy)propionitrile
发明人：TAKAHASHI SATOMI; UEDA YASUYOSHI; SHIMADA YOSHIO; WATANABE KIYOSHI
权利人:KANEGAFUCHI CHEMICAL IND
摘要:The present invention relates to 3-(4-fluorophenoxy)propionitrile having the formula (I): (I) a process for preparing 3-(4-fluorophenoxy)propionitrile having the formula (I) which comprises reacting 4-fluorophenol and acrylonitrile in the presence of a tertiary amine, a process for preparing 6-fluoro-4-chromanone having the formula (II): (II) which comprises reacting 3-(4-fluorophenoxy)propionitrile having the formula (I) with an acid, and a process for preparing 6-fluoro-4-chromanone having the formula (II) which comprises reacting 4-fluorophenol with acrylonitrile in the presence of a catalyst to give 3-(4-fluorophenoxy)propionitrile having the formula (I), which is then reacted with an acid. 6-Fluoro-4-chromanone is an important intermediate for the synthesis of (S)-2,3-dihydro-6-fluoro-spiro[4H-1-benzopyran-4,4'-imidazolidine]-2', 5'dione (USAN: sorbinil).