Sagami Chemical Research Center

Nissan Chemical Industries Limited

Toyo Stauffer Chemical Co., Ltd.

Toyo Jozo Company, Ltd.

Genichi Tsuchihashi

Katsuyuki Ogura

Shuichi Mitamura

Ryozo Sakoda

Keisuke Suzuki

Isao Hashiba

Tadashiro Fujii

Shuichi Fukushima

Kazuo Nagano

Koji Kitajima

Tetsuo Watanabe

Yumiko Ando

Masashi Kuramoto

Kumi Kobayashi

Masao Yaso

A preparing method of optically active ketones given by a general formula ##STR1## (wherein R represents a hydrocarbon group having 2 to 20 carbon atoms and R' represents a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon groups of R and R' may contain functional groups having no influence on the reaction. But, * represents an asymmetric carbon atom, and R represents a more electron donating group than R' (except when R=R') through the rearrangement reaction by using organoaluminum compound.

Preparing method of optically active ketones

A method of preparing optically active ketones having the general formula ##STR1## wherein R.sup.2 and R.sup.3 indicate hydrocarbon groups having 1 to 20 carbon atoms characterized by submitting an optically active sulfonyloxy alcohol having the general formula ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 indicate hydrocarbon groups having carbon atoms of 1 to 20 and which optionally contain N, O, P and S. The symbol * indicates asymmetric carbon atoms to rearrangement in a solvent and in the presence of organoaluminum compounds given by the general formula R.sub.3-n.sup.4 AlX.sub.n, (wherein R.sup.4 indicates an alkyl group having carbon atoms of 1 to 20 and X indicates a halogen atom, an alkoxy group or a CN group. n is 1, 1.5 or 2).

Method of preparing optically active ketones

A manufacturing method is described for the preparation of optically active 1-(6-methoxy-2-naphthyl)-2-(alkoxycarbonyl)amino-1-propanone, its derivatives and their halo analogs. The optically active 1-(6-methoxy-2-naphthyl)-2-(alkoxycarbonyl)amino-1-propanone, its derivatives and their halo analogs are useful intermediates in the preparation of 2-(6-methoxy-2-naphthyl)propionic acid, which is useful as pharmaceutical, e.g. antiinflammatory, analgesic and anti-pyretic agents.

Optically active 1-(6-methoxy-2-naphthyl)-2-(alkoxycarbonyl)

An alpha-thio-alpha-aryl-substituted alkanonitrile of the general formula ##STR1## wherein Ar represents an aromatic group, R represents a hydrogen atom or an alkyl group, R.sup.1 represents an alkyl group or an aromatic group, and Y represents an oxygen atom or a carbonyl group. The above compound can be prepared by reacting an alpha-aryl-substituted-alpha-thio-acetonitrile of the general formula ##STR2## wherein Ar, Y and R.sup.1 are as defined above, with an alkylating agent in the presence of a strong base. This compound is useful as an intermediate for producing an alpha-aryl-substituted alkane-carboxylic acid of the general formula ##STR3## wherein Ar, Y and R.sup.1 are as defined above.

Alpha-thio-alpha-aryl-substituted alkanonitrile and process for

Novel .alpha.-thio-alkanoic acid derivatives and a process for their preparation. These novel compounds can be easily converted to useful medicines.

Novel .alpha.-thio-alkanoic acid derivatives

An o-(N-allyl-2,6-dichloroanilino)phenylacetic acid derivative represented by the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3, which may be the same or different, individually represent a hydrogen atom, a halogen atom or an alkyl group; Y represents a hydroxyl group, an alkoxyl group, a --OM.sup.1 group in which M.sup.1 is an alkali metal atom, a --OM.sub.1/2.sup.2 group in which M.sup.2 is an alkaline earth metal atom, an amino group having the formula --NR.sup.5 R.sup.6 in which R.sup.5 and R.sup.6, which may be the same or different, individually represent a hydrogen atom or an alkyl group, or a hydroxylamino group, and processes for preparing the same.

O-(N-Allyl-2,6-dichloroanilino)phenylacetic acid derivative and a

Aromatic acetic acid derivatives having a sulfur atom at the alpha-position, and a process for their preparation. Useful drugs can be produced from derivatives. erivatives.

Aromatic acetic acid derivatives having sulfur atom at alpha-position

Novel compounds of [N-benzyl-o-(2,6-dichloroanilino)phenyl]acetic acid derivatives having the formula ##STR1## wherein X represents H, Cl, Br or a C.sub.1 -C.sub.4 alkyl group and Y is OH, OR or SR and R represents a C.sub.1 -C.sub.4 alkyl group.

[N-benzyl-o-(2,6-dichloroanilino)phenyl]acetic acid derivatives

Aromatic acetic acid derivatives having a sulfur atom at the alpha-position, and a process for their preparation. Useful drugs can be produced from these derivatives.

Cephalosporins having a sulfur-containing functional group of the formula ##STR1## present at the carbon atom directly bonded to the thienyl or furyl group in the side chain of the 7-position of cephem derivatives. These compounds are useful as anti-bacterial agents against Gram-positive and Gram-negative bacteria.

Cephalosporins having a sulfur containing functional group in the

Commercially advantageous processes for preparing thienylacetic acid, furylacetic acid or alkyl esters of these. Novel thiophene or furan derivatives that can be used as starting materials for preparing the above compounds. Processes for preparing these starting materials are also provided.

Thioprene or furan derivatives and process for preparation thereof

Thiophene derivatives and process for preparation thereof

A novel sulfoxide derivative of the general formula ##STR1## wherein R.sup.1 and R.sup.3 are the same or different, and each represents and alkyl group having 1 to 4 carbon atoms, a phenyl group or a halo- or methyl-substituted phenyl group, R.sup.2 is a hydrogen atom, a lower alkyl group, benzyl group, or a p-methoxy- or p-bromo-benzyl group, R.sup.1 and R.sup.2, together, may form an alkylene group containing 3 carbon atoms, and X is an oxygen or sulfur atom, and to a process for its preparation.

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Tama, Japan

Genichi Tsuchihashi