Industrial Technology Research Institute

Ching-Te Chang

Rong-Tsun Wu

Chen-Tao Lee

Fen-Lan Lin

Fueng-Lan Lin

Wann-Huang Liu

Kuo-Mou Chen

Lian-Tze Lee

Hsueh-Ling Su

Tsung-Tsan Su

A method of augmenting the immune system including administering to a subject an effective amount of a compound of the following formula: ##STR1## wherein m is 1-4; and each of A and B, independently, is H, C.sub.1-7 alkyl, C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, (CH.sub.2).sub.n CHO, (CH.sub.2).sub.o COOH, C.sub.1-7 alkoxy, C.sub.2-7 alkoxyalkyl, C.sub.1-7 hydroxyalkyl, CN, NO.sub.2, halogen, CH(OR.sup.1).sub.2, CO.R.sup.1, NR.sup.2 R.sup.3 or its acid salt, CO.NR.sup.2 R.sup.3, CHR.sup.1 NR.sup.2 R.sup.3 or its acid salt, CH.dbd.NR.sup.2, C.tbd.CR.sup.4, CR.sup.1 .dbd.CR.sup.5 R.sup.6, CO.CH.dbd.CHR.sup.7, CH.dbd.CHR.sup.8, or COOR.sup.9 ; in which each of n and o, independently, is 0-4; R.sup.1 is C.sub.1-4 alkyl or C.sub.1-4 acyl; each of R.sup.2 and R.sup.3, independently, is H, C.sub.1-4 alkyl, or C.sub.1-4 hydroxyalkyl; R.sup.4 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, COR.sup.2, COOR.sup.10, C.sub.1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C.sub.1-4 dihydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C.sub.1-4 halogenated alkyl; OR.sup.1, or NHR.sup.7 ; each of R.sup.5 and R.sup.6, independently, is H, CHO, COR.sup.1, COOH, COOR.sup.9, CN, or halogen; R.sup.7 is H, C.sub.1-4 alkyl, 2-thienyl, phenyl, mono-substituted phenyl, or di-substituted phenyl; R.sup.8 is COOR.sup.2, CO.CHO, C.sub.1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether; and R.sup.9 is H, C.sub.1-4 alkyl, phenyl, mono-substituted phenyl, di-substituted phenyl, or 2-thienyl.

Medicinal thiophene compounds

A method of treating tumor including administering to a subject an effective amount of a compound of the following formula: ##STR1## wherein m is 1-4; and each of A and B, independently, is H, C.sub.1-7 alkyl, C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, (CH.sub.2).sub.n CHO, (CH.sub.2).sub.o COOH, C.sub.1-7 alkoxy, C.sub.2-7 alkoxyalkyl, C.sub.1-7 hydroxyalkyl, CN, NO.sub.2, halogen, CH(OR.sup.1).sub.2, CO.R.sup.1, NR.sup.2 R.sup.3 or its acid salt, CO.NR.sup.2 R.sup.3, CHR.sup.1 NR.sup.2 R.sup.3 or its acid salt, CH.dbd.NR.sup.2, C.tbd.CR.sup.4, CR.sup.1 .dbd.CR.sup.5 R.sup.6, CO.CH.dbd.CHR.sup.7, CH.dbd.CHR.sup.8, or COOR.sup.9 ; in which each of n and o, independently, is 0-4; R.sup.1 is C.sub.1-4 alkyl or C.sub.1-4 acyl; each of R.sup.2 and R.sup.3, independently, is H, C.sub.1-4 alkyl, or C.sub.1-4 hydroxyalkyl; R.sup.4 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, COR.sup.2, COOR.sup.10, C.sub.1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C.sub.1-4 dihydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C.sub.1-4 halogenated alkyl; OR.sup.1, or NHR.sup.7 ; each of R.sup.5 and R.sup.6, independently, is H, CHO, COR.sup.1, COOH, COOR.sup.9, CN, or halogen; R.sup.7 is H, C.sub.1-4 alkyl, 2-thienyl, phenyl, mono-substituted phenyl, or di-substituted phenyl; R.sup.8 is COOR.sup.2, CO.CHO, C.sub.1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether; and R.sup.9 is H, C.sub.1-4 alkyl, phenyl, mono-substituted phenyl, di-substituted phenyl, or 2-thienyl.

Novel hydroxymethylthiophene derivatives and their medical use in treating or preventing inflammation and edema.

Hydroxymethylpolythiophene derivatives

A method of treating inflammation including administering to a subject an effective amount of a compound of the following formula: ##STR1## wherein m is 1-4; and each of A and B, independently, is H, C.sub.1-7 alkyl, C.sub.2-7 alkenyl, C.sub.2-7 alkynyl, (CH.sub.2).sub.n CHO, (CH.sub.2).sub.o COOH, C.sub.1-7 alkoxy, C.sub.2-7 alkoxyalkyl, C.sub.1-7 hydroxyalkyl, CN, NO.sub.2, halogen, CH(OR.sup.1).sub.2, CO.R.sup.1, NR.sup.2 R.sup.3 or its acid salt, CO.NR.sup.2 R.sup.3, CHR.sup.1 NR.sup.2 R.sup.3 or its acid salt, CH=NR.sup.2, C.tbd.CR.sup.4, CR.sup.1 =CR.sup.5 R.sup.6, CO.CH.dbd.CHR.sup.7, CH.dbd.CHR.sup.8, or COOR.sup.9 ; in which each of n and o, independently, is 0-4; R.sup.1 is C.sub.1-4 alkyl or C.sub.1-4 acyl; each of R.sup.2 and R.sup.3, independently is H, C.sub.1-4 alkyl, or C.sub.1-4 hydroxyalkyl; R.sup.4 is H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, COR.sup.2, COOR.sup.10, C.sub.1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C.sub.1-4 dihydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether, C.sub.1-4 halogenated alkyl; OR.sup.1, NHR.sup.7 ; each of R.sup.5 R.sup.6, independently, is H, CHO, COR.sup.1, COOH, COOR.sup.9, CN, or halogen; R.sup.7 is H, C.sub.1-4 alkyl, 2-thienyl, phenyl, mono-substituted phenyl, or di-substituted phenyl; R.sup.8 is COOR.sup.2, CO.CHO, C.sub.1-4 hydroxyalkyl or its acid ester or 2-tetrahydropyranyl ether; and R.sup.9 is H, C.sub.1-4 alkyl, phenyl, mono-substituted phenyl, di-substituted phenyl, or 2 -thienyl.

A pharmaceutical composition containing a compound and an excipient, the compound having the formula: ##STR1## in which n is 2, 3 or 4; R is H, --CH(R.sup.1).cndot.OR.sup.2, --CH(O--Z).sub.2, or --COR.sup.3 ; R.sup.1 is H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, OH, C.sub.1-6 hydroxyalkyl, or COOH; R.sup.2 is H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, tetrahydropyranyl, phenyl, benzoyl, C.sub.1-6 acyl, tosyl, or --CO--Y--COOH; and R.sup.3 is H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, OH, C.sub.1-6 hydroxyalkyl, or COOH; wherein Z is C.sub.1-6 alkyl, C.sub.2-6 alkenyl, or C.sub.1-6 acyl; and Y is C.sub.1-6 alkylidene, C.sub.2-6 alkenylidene, phenylene, or deleted; or an ester or a salt thereof.

Hydroxymethyl-polythiophene derivatives

Hydroxymethypolythiophene derivatives

Reaction mixture of germanium dioxide and hypophosphorous acid or its salts in hydrochloric acid is extracted with organic solvent. This resultant is then reacted with acrylic acid or its derivatives, and further hydrolyzed to provide bis-carboxy ethyl germanium sesquioxide or its propionic acid derivatives.

Preparation of bis-carboxy ethyl germanium sesquioxide and its propionic

Germanium tetrachloride is reduced with hypophosphorous acid or its salt in hydrochloric acid, or lower alcohol, or lower alcoholic hydrochloric acid solution. The reaction mixture is then reacted with acrylic acid derivatives and further hydrolyzed to the desired organo germanuim propionic acid derivatives.

Method for preparing organo germanium propionic acid derivatives

Compounds of the formula ##STR1## or pharmaceutically acceptable acid addition salts thereof (for example, a chloride) are useful as local anesthetics. In the compound of the formula (I), R is hydrogen or C.sub.1 -C.sub.14 alkyl, ALK is C.sub.1 -C.sub.4 alkylene, R.sub.1 and R.sub.2 may be the same or different and are hydrogen or C.sub.1 -C.sub.6 alkyl or R.sub.1 and R.sub.2 taken together form a 5 to 7 atom ring which contains 1 to 2 nitrogen atoms.

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Taipei, Taiwan

Ching-Te Chang