Daicel Chemical Industries, Ltd.

Fujisawa Pharmaceutical Company, Ltd.

Other

Yoshiyuki Murai

Masahiro Nishikawa

Noritsugu Yamasaki

Yoichiro Ueda

Takafumi Imoto

Ichiro Takase

Teruo Kyoto Oku

Takahiro Hiramura

Kouzou Sawada

Osamu Onomura

Kunihiko Dohtsu

3-(2,4-Dichlorobenzyl)-2-methyl-N-(pentylsulfonyl)-3H-benzimidazole-5-carboxamide, a compound having hypoglycemic activity or PDE5 inhibitory effect, has three forms of crystal forms that are distinguishable by their X-ray powder diffraction values. The most crystallographically stable crystal form is useful as a drug substance for medicines. Another crystal form can be purified efficiently by crystallization, since it forms larger crystals and can be very easily isolated by filtration. Thus this crystal form is useful for purifying 3-(2,4-Dichlorobenzyl)-2-methyl-N-(pentylsulfonyl)-3H-benzimidazole-5-carboxamide.

Crystal forms of 3-(2,4-dichlorobenzyl)-2-methyl-n-(pentylsulfonyl)-3h-benzimidazole-5-carboxamide

Benzimidazole compounds

Benzimidazole derivatives

A purified acid addition salt of a (2S, 3S, 5S)-2,5-diamino-1,6-diphenyl-3-hydroxyhexane, e.g., (2S, 3S, 5S)-2-tert-butoxycarbonylamino-3-hydroxy-5-amino-1,6-diphenylhexane, is obtained from its mixture, in an arbitrary ratio, with its (2S, 3S, 5R) stereoisomer in the presence of an inorganic or organic acid. The desired (2S, 3S, 5S) acid addition salt may be recovered from the mixture by, for example, recrystallization. These purified acid addition salts are useful as intermediates in the synthesis of medicines such as retrovirus protease inhibitors including human immunodeficiency virus (HIV) protease inhibitors.

2-isoxazoline derivative and process for producing the same and process

The invention provides methods for preparing a 2-isoxazoline compound represented by formula (1) and a 2,5-diamino-1,6-diphenyl-3-hydroxyhexane compound obtainable by reducing the 2-isoxazoline compound and represented by formula (6): ##STR1## wherein Ph is phenyl; and each of R.sup.1 and R.sup.2 independently represents hydrogen, acyl, alkyloxycarbonyl, arylalkyloxycarbonyl, aryloxycarbonyl, alkylaminocarbonyl, arylalkylaminocarbonyl, arylaminocarbonyl, alkyl, arylalkyl, aryl, alkylsulfonyl, acylalkylsulfonyl, or arylsulfonyl, or R.sup.1 and R.sup.2 are linked to each other to form divalent acyl. These compounds are useful as intermediates in the synthesis of medicines such as retrovirus protease inhibitors including human immunodeficiency virus (HIV) protease inhibitors.

2-isoxazoline derivative and process for producing the same; and process

2-isoxazoline derivative and process for producing the same, and process

Growing community of inventors

Hyogo, Japan

Yoshiyuki Murai