Shionogi Company Limited

Tsutomu Sugasawa

Kazuyuki Sasakura

Makoto Adachi

Tatsuo Toyoda

Hiromu Matsumura

Akira Takase

Masami Eigyo

Akira Matsushita

Shinzaburo Sumimoto

Ichiro Ishizuka

Akira Noto

Shiro Ueda

Kunihiro Nakajima

Katsuto Okuno

Adachi Makoto

Highly sensitive reagent for colorimetrically determining N-acetyl-.beta.-D-glucosaminidase (NAGase) activity by the continuous method, comprising sodio-3,3'-dichlorophenolsulfonphthaleinyl N-acetyl-.beta.-D-glucosaminide and a buffer, with which renal dysfunction can be diagnosed precisely, quickly, and easily.

Method for determination of nagase and reagent therefor

A process for introducing thiocarboxylic ester at ortho-position of phenols or phenylamines which comprises reacting a phenyl compound having group or optionally substituted amino or cyclic amino group, of which at least one ortho-position is vacant, with C.sub.1 -C.sub.5 alkyl thiocyanate, C.sub.7 -C.sub.13 aralkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and hydrolyzing the resultant product under acidic conditions is provided, and said process is useful in the synthesis of medicinals, pesticides and dyes.

Process for introducing a thiocarboxylic ester group at the

Novel ortho-(mono-substituted amino)phenylimines being intermediates to psychotropic drugs and other drugs are economically and industrially prepared by reacting anilines with nitriles in the presence of a boron trifluoride ether adduct and a halide-type Lewis acid, if necessary together with an organic base. Furthermore, the imines can be hydrolyzed with an acid to afford the corresponding ketones.

Ortho-mono-substituted amino)phenylimines

A process for ortho-cyanation of phenols or phenylamines which comprises reacting a phenyl compound having hydroxy or optionally substituted amino or cyclic amino, of which ortho position is vacant, with trichloroacetonitrile, C.sub.1 -C.sub.5 alkyl thiocyanate or C.sub.6 -C.sub.12 aryl thiocyanate in the presence of a boron trihalide and treating the resultant product with an alkali is provided, and said process is useful in the synthesis of intermediates for medicinals or pesticides.

Process for ortho-cyanation of phenols or phenylamines

Improvement in the production of psychotropic 1-substituted-1,3-dihydro-1,4-benzodiazepin-2-ones starting from 2-(1-substituted)amino-benzophenonimines through novel intermediates of the formula: ##STR1## (wherein R is hydrogen, methyl or benzyl, R.sup.1 is C.sub.1 -C.sub.5 alkyl or phenyl-C.sub.1 -C.sub.5 alkyl, X and Y each is hydrogen or halogen and n is an integer of 1 to 2) with economical and industrial advantage.

Process for preparing 1-substituted-1,4-benzodiazepine derivatives

1,4-Benzodiazepine derivatives of the formula: ##STR1## (in which R.sup.1 is pyrrolidinyl or piperidinyl each optionally substituted by C.sub.1-3 alkyl, phenyl-C.sub.1-3 alkyl, C.sub.1-5 alkanoyl, or C.sub.2-5 alkoxycarbonyl,

1,4-Benzodiazepine derivatives

Process for production of 2-haloacetylphenols

Process for the production of o-(N-monosubstituted amino)benzyl alcohols which comprises reacting an N-mono-substituted aniline optionally having one or more substituents with a boron trihalogenide at a temperature from about 0.degree. C. to about 100.degree. C. and reacting the resultant boron compound with an aldehyde in the presence of a base at a temperature from about -30.degree. C. to about 100.degree. C. to regiospecifically introduce a 1-hydroxy-alkyl or 1-hydroxy-substituted alkyl group into the ortho position of said aniline.

Process for the production of o-(N-monosubstituted amino)benzyl alcohols

Cyanopinacolone is produced by reacting pinacolone with about 1.0 to about 1.2 molar equivalents of chlorine in methanol and further reacting the resulting monochloropinacolone with about 1.0 to about 1.2 molar equivalents of an alkali metal cyanide in methanol.

Process for the production of cyanopinacolone

O-Aminophenyl ketone derivatives are regio-specifically prepared by reacting an aniline unsubstituted in at least one ortho position with a nitrile in the presence of boron trihalogenide to introduce a substituted iminomethyl into the ortho position of said aniline and hydrolyzing the resulting iminomethyl compound.

Process for the production of o-aminophenyl ketone derivatives

Camptothecin analogues showing more potent anti-tumor activity than a naturally occurring alkaloid camptothecin, which also exhibit an immunosuppressive activity, in which the 1-ethyl of camptothecin is replaced by various members of substitutents such as alkyls (except ethyl), alkenyls, alkynyls, aralkyls or aryloylalkyls; being produced from readily accessible starting materials on totally synthetic method newly developed by the present inventor.

Growing community of inventors

Hyogo, Japan

Tsutomu Sugasawa