Tanabe Seiyaku Company, Limited

Muneyoshi Ikezaki

Taku Nagao

Hiromichi Nakajima

Nobuo Ito

Masao Hoshiyama

Masanori Inamasu

Yasushi Okazaki

Hajime Iwai

Norihide Umino

Masanori Sato

Katsuo Ikezawa

Takeshi Kanno

Katsuyuki Noguchi

Tokuro Ohishi

Yashushi Okazaki

Hisao Otsuka

Kunihiko Irie

Takashi Morita

A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, halogen or alkoxy having one to four carbon atoms, and Ring A is the same as defined above, to give a compound of the formula: ##STR3## wherein R' and Ring A are the same as defined above, and when R' is benzyloxy, if required, further subjecting the compound [I'] to catalytic hydrogenation to give a compound of the formula: ##STR4## wherein Ring A is the same as defined above. The benzylalcohol derivative [I] is useful as an anti-diabetic agent.

Benzylalcohol derivative and process for preparing

A compound of the formula: ##STR1## wherein R is alkanoyl of one to 20 carbon atoms, benzoyl or lower alkyl-benzoyl, and processes for preparation thereof are disclosed. Said compound (I) and a pharmaceutically acceptable acid addition salt thereof are useful as a cardiotonic agent.

Novel benzylalcohol derivatives and processes for preparing same

A benzylalcohol derivative of the formula: ##STR1## wherein R is hydroxy, benzyloxy, alkoxy of one to 4 carbon atoms or halogen, and Ring A is monomethoxyphenyl, dimethoxyphenyl, trimethoxyphenyl or 3,4-methylenedioxyphenyl is prepared by reducing a compound of the formula: ##STR2## wherein R' is benzyloxy, alkoxy of one to 4 carbon atoms or halogen, and Ring A is the same as defined above, and when R' is benzyloxy, if required, further subjecting the product to catalytic hydrogenation. The compounds (I) and pharmaceutically acceptable acid addition salts thereof are used as anti-diabetic agents.

Novel benzylalcohol derivative and process for preparing the same

Racemic or optically active .alpha.-(2,3,4-trimethoxyphenethylaminomethyl)-2-hydroxybenzylalcohol [I] may be prepared by condensing 2,3,4-trimethoxyphenethylamine with 2-benzyloxyphenylglyoxal or its hydrate, reducing the resultant .alpha.(2,3,4-tri-methoxyphenethylimino)-2-benzyloxyacetophenone to give .alpha.(2,3,4-trimethoxyphenethylaminomethyl)-2-benzyloxybenzylalcohol, if required, resolving the 2-benzyloxybenzylalcohol derivative into each of its optically active enantiomers, and subjecting the racemic modification or optically active enantiomer of said 2-benzyloxybenzylalcohol derivative to catalytic hydrogenation. The compound [I] and pharmaceutically acceptable acid addition salts thereof are useful as anti-diabetic agents. They may be also used in the treatment of thrombosis.

Novel benzylalcohols and pharmaceutical compositions and use thereof

A compound of the formula: ##STR1## wherein R is lower alkyl, may be prepared, for example, by reducing a compound of the formula: ##STR2## wherein R is same as above. Other methods for preparing the compound [I] are also disclosed. The compound [I] and a pharmaceutically acceptable acid addition salt thereof are useful as anti-diabetic agents.

Novel benzylalcohol derivatives and processes for preparing the same

A compound having the formula: ##STR1## wherein Ring A is monohydroxyphenyl, or a pharmaceutically acceptable acid addition salt thereof is prepared by catalytic hydrogenation of a compound having the formula: ##STR2## wherein A' is monobenzyloxyphenyl, and Y is carbonyl or hydroxymethylene. The compound (I) in which Ring A is 4-hydroxyphenyl or 3-hydroxyphenyl is useful as a cardiotonic agent. On the other hand, the compound (I) in which Ring A is 2-hydroxyphenyl is useful as an anti-diabetic agent.

Novel benzylalcohol derivatives as antidiabetics and cardiotonics

A novel 5,7-dihydroxytetrahydroisoquinoline derivative having the formula: ##STR1## wherein R is trimethoxyphenyl, is prepared either by hydrolysis of a compound having the formula: ##STR2## wherein R.sup.1 is an organic acyl group and R is same as above, or by catalytic hydrogenation of a compound having the formula: ##STR3## wherein R.sup.3 is hydrogen or benzyl and R is same as above. The 5,7-dihydroxytetrahydroisoquinoline derivative (I) or a pharmaceutically acceptable acid addition salt thereof is useful as a bronchodilator.

5,7 Dihydroxy-1-(trimethoxybenzyl)-1,2,3,H-tetrahydroisoquinolines and

Benzylalcohol amine derivatives

A compound of the formula: ##SPC1## Wherein Ring A' is dibenzyloxyphenyl and Y is carbonyl or hydroxymethylene, is subjected to catalytic hydrogenation. A compound of the formula: ##SPC2## Wherein Ring A is dihydroxyphenyl, is produced. The product is useful as a cardiotonic agent. It is also characterized by the high potency ratio of adrenergic .beta..sub.1 -receptor stimulating activity to adrenergic .beta..sub.2 -receptor stimulating activity.

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Ageo, Japan

Muneyoshi Ikezaki