Nissan Chemical Industries Limited

Sagami Chemical Research Center

Ryozo Sakoda

Kiyotomo Seto

Keizo Tanikawa

Hiroo Matsumoto

Ken-ichi Shikada

Sakuya Tanaka

Yoshimasa Kamikawaji

Nobutomo Tsuruzoe

Takashi Matsumoto

Akira Saito

Norimasa Shudo

Motoo Mutsukado

Shin-ichi Akiyama

Katsuyuki Ogura

Genichi Tsuchihashi

Yoshihiro Fujikawa

Mitsuaki Sakashita

Isao Hashiba

Kazuhiko Ohrai

Tadashi Sasaki

Yukinori Masuda

Kazuo Nagano

Morihide Hibi

Koichi Maeda

Hideki Takamatsu

Keisuke Ohdoi

Shuichi Fukushima

Kyoko Nakayama

Yumiko Ando

An agent for enhancing the drug effects of an antitumor drug, which comprises a compound of the formula I: ##STR1## or a pharmaceutically acceptable salt of the compound.

Phosphorus pyridine compound

A compound of the formula, ##STR1## or its pharmaceutically acceptable salt, and its preparation process and pharmaceutical compositions characterized by containing these compounds as effective ingredients. These compounds have strong antithrombotic activity, cardiotonic activity, vasodilator activity and anti-SRS-A activity, and are useful as prophylactic or therapeutic agents for various thrombotic affections, congestive heart failure, hypertension, asthma, immediate type allergy diseases and the like.

5-heteroarylamino-6-oxy-substituted 3(2H)-pyridazinones

A process for the optical resolution of a pyranobenzoxadiazole compound represented by the formula [(.+-.)I]: ##STR1## which comprises reacting the compound [(.+-.)I] with an optically active carboxylic acid represented by the formula [II]: ##STR2## and separating the diastereomeric salt thus formed is disclosed.

Process for the optical resolution of pyranobenzoxadiazole compounds

A compound of the formula: ##STR1## or its pharmaceutically acceptable salt and pharmaceutical compositions containing these compounds as effective ingredients. These compounds have strong antithrombotic activity, cardiotonic activity, vasodilator activity and anti-SRS-A activity, and are useful as prophylactic or therapeutic agents for various thrombotic afflictions, congestive heart failure, hypertension, asthma, immediate-type allergy diseases and the like.

Compounds of the formula (I): ##STR1## in which the nitrogen-containing hetero ring portion is 1,4-dihydropyridine ring or a pyridine ring, R.sup.1 is only present when the nitrogen-containing hetero ring is a 1,4-dihydropyridine ring, and Z is a group of the formula (II): ##STR2## in which R.sup.4 and R.sup.5 may be the same or different and together may form one divalent group, are effective agents for enhancing the antitumor effect of antitumor drugs.

Drug effect-enhancing agent for antitumor drug

A compound of the formula (I): ##STR1## wherein X.sup.1 and X.sup.2 do not exist or represent oxygen atom; A represents OH or acyloxy group having 1 to 4 carbon atoms; B represents hydrogen atom; A and B together represent a bond; R.sup.1 and R.sup.2 represent hydrogen atom or alkyl group having 1 to 4 carbon atoms, or R.sup.1 and R.sup.2 together represent 1,2-ethylene, 1,3-propylene, 1,4-butylene or 1,5-pentylene, and these alkylene groups may be substituted by alkyl group having 1 to 4 carbon atoms; R.sup.3 represents amido group of the formula: ##STR2## wherein n, R.sup.4, R.sup.5, R.sup.6, R.sup.7. R.sup.8. R.sup.9, R.sup.10 and R.sup.11 represent specific groups, and the pharmacological acceptable salts of the compounds which can form salts have strong activity for lowering blood pressure, and process therefor and pharmaceutical use of the compounds.

Pyranobenzoxadiazole derivatives

5-arylmethylamino-6-oxy-substituted 3(2H)-pyridazinones

A hydrazine derivative having the formula: ##STR1## wherein R is a hydrogen atom or ##STR2##

Hydrazine derivatives useful as intermediates in the synthesis of

Compounds of the formula (I): ##STR1## in which the nitrogen-containing hetero ring portion is a 1,4-dihydropyridine ring or a pyridine ring, R.sup.1 is only present when the nitrogen-containing hetero ring is a 1,4-dihydropyridine ring, and Z is either a CO.sub.2 R.sup.8 group or a group of the formula (II): ##STR2## in which R.sup.4 and R.sup.5 may be the same or different and together may form one divalent group, are effective agents for enhancing the antitumor effect or antitumor drugs.

A thin platinum film is formed on a substrate of glass, alumina or pottery by applying on the surface of the substrate a solution containing one part by weight of an organic platinum complex represented by formula (I):

Thin platinum film-forming composition

A 3(2H)pyridazinone of the formula: ##STR1## wherein R.sub.1 is C.sub.2 -C.sub.5 alkyl; R.sub.2 is hydrogen, C.sub.1 -C.sub.3 alkyl, chlorine or bromine; R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; and each of Y.sub.1, Y.sub.2 and Y.sub.3 which may be the same or different, is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, halogen, --(CH.sub.2).sub.l A [wherein A is substituted amino of the formula --N(R.sub.4) (R.sub.5) (wherein each of R.sub.4 and R.sub.5 which may be the same or different, is C.sub.1 -C.sub.4 alkyl, or R.sub.4 and R.sub.5 together form C.sub.4 -C.sub.6 alkylene), morpholino, 4-R.sub.6 -piperazin-1-yl (wherein R.sub.6 is C.sub.1 -C.sub.3 alkyl) or --OR.sub.7 (wherein R.sub.7 is hydrogen or C.sub.1 -C.sub.3 alkyl), and l is an integer of 0 to 3], --OR.sub.8 [wherein R.sub.8 is hydrogen, C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.5 alkenyl, benzyl or --(CH.sub.2).sub.q --R.sub.9 [wherein R.sub.9 is CO.sub.2 R.sub.3 (wherein R.sub.3 is as defined above), --CONHR.sub.3 (wherein R.sub.3 is as defined above) or --CH.sub.2 OR.sub.7 (wherein R.sub.7 is as defined above), and q is an integer of 1 to 5]], --CO.sub.2 R.sub.3 (wherein R.sub.3 is as defined above), --CON(R.sub.10) (R.sub.11) [wherein each of R.sub.10 and R.sub.11 which may be the same or different, is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.5 alkenyl, or R.sub.10 and R.sub.11 together form C.sub.4 -C.sub.6 alkylene, --(CH.sub.2).sub.2 O(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 N(R.sub.6)(CH.sub.2).sub.2 -- (wherein R.sub.6 is as defined above)], --CONH(CH.sub.2).sub.m A (wherein A is as defined above, and m is an integer of 2 to 4), --CH.dbd.CHCOR.sub.12 (wherein R.sub.12 is hydroxy, C.sub.1 -C.sub.4 alkoxy or --N(R.sub.13) (CH.sub.2).sub.n CO.sub.2 R.sub.3 (wherein R.sub.13 is hydrogen, C.sub.1 -C.sub.6 alkyl or cycloalkyl, R.sub.3 is as defined above, and n is an integer of 1 to 4)), --SR.sub.14 (wherein R.sub.14 is C.sub.1 -C.sub.4 alkyl), --CN or ##STR2## wherein R.sub.3 is as defined above), or two of Y.sub.1, Y.sub.2 and Y.sub.3 together form ##STR3## (wherein p is an integer of 1 or 2), and a pharmaceutically acceptable salt thereof.

3(2H)pyridazinone, process for its preparation and anti-allergic agent

A 3(2H)pyridazinone of the formula: ##STR1## wherein R.sub.1 is hydrogen, 2-propenyl or straight chained or branched C.sub.1 -C.sub.4 alkyl; R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl; X is chlorine or bromine; Y is hydrogen, nitro, -NHR.sub.3 wherein R.sub.3 is hydrogen or straight chained or branched C.sub.1 -C.sub.4 alkyl, -AR.sub.4 wherein A is oxygen or sulfur and R.sub.4 is hydrogen, straight chained or branched C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl having one double bond, C.sub.3 -C.sub.6 alkynyl having one triple bond, phenyl or ##STR2## wherein R.sub.5 is hydrogen or C.sub.1 -C.sub.4 alkyl, or halogen; Z.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, -OR.sub.6 wherein R.sub.6 is hydrogen, straight chained or branched C.sub.1 -C.sub.8 alkyl or ##STR3## wherein n is an integer of from 1 to 4, -N(R.sub.7).sub.2 wherein R.sub.7 is C.sub.1 -C.sub.4 alkyl, or halogen; Z.sub.2 is C.sub.1 -C.sub.4 alkyl, -OR.sub.6 wherein R.sub.6 is as defined above, -N(R.sub.7).sub.2 wherein R.sub.7 is as defined above, or halogen, provided that when R.sub.1 is straight chained or branched C.sub.2 -C.sub.4 alkyl, Y is not hydrogen and when R.sub.1 is hydrogen, methyl or 2-propenyl, Y and R.sub.2 are not simultaneously hydrogen, or a pharmaceutically acceptable salt thereof.

3(2H)pyridazinone, and antagonistic agent against SRS-A containing it

A compounds of the formula (I): ##STR1## wherein A represents OH or OC(O)CH.sub.3-n X.sub.n, B represents hydrogen atom, or A and B together represent a bond; R.sup.1 represents hydrogen atom, R.sup.2 represents hydrogen atom, C(Z)CH.sub.3-n X.sub.n or C(Z)NHCH.sub.3-n X.sub.n or R.sup.1 and R.sup.2 together represents (CH.sub.2).sub.m, (CH.sub.2).sub.m-1 C(Z), N(R.sup.3)(CH.sub.2).sub.2 C(Z), (CH.sub.2).sub.m-2 NHC(Z) or (CH.sub.2).sub.m-2 OC(Z) in which X represents fluorine atom, chlorine atom, bromine atom, a methyl group or a methoxy group and n represents 0 or an integer of 1 to 3, Z represents oxygem atom or sulfur atom, m represents an integer of 4 or 5 and R.sup.3 represents hydrogen atom or a methyl group, and pharmacological acceptable salts of the compounds which can form salts, processes therefor and pharmaceutical use of the compounds.

A 3(2H)pyridazinone of the formula: ##STR1## wherein R.sub.1 is hydrogen, methyl, C.sub.3 -C.sub.6 alkenyl, C.sub.5 or C.sub.6 cycloalkyl, benzyl, phenyl, --(CH.sub.2).sub.m CO.sub.2 R.sub.3 (wherein R.sub.3 is hydrogen or C.sub.1 -C.sub.5 alkyl, and m is an integer of from 1 to 4), --(CH.sub.2).sub.n A (wherein A is --OH or --N(R.sub.4).sub.2 wherein R.sub.4 is C.sub.1 -C.sub.3 alkyl, and n is an integer of from 2 to 6) or --CH.sub.2 CF.sub.3 ; R.sub.2 is chlorine or bromine; each of Y.sub.1 and Y.sub.2 which may be the same or different, is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.8 alkenyl, halogen, --OR.sub.5 (wherein R.sub.5 is hydrogen, C.sub.1 -C.sub.8 alkyl or ##STR2## wherein q is an integer of from 1 to 4), --CO.sub.2 R.sub.6 (wherein R.sub.6 is hydrogen or C.sub.1 -C.sub.5 alkyl), --N(R.sub.7).sub.2 (wherein R.sub.7 is C.sub.1 -C.sub.4 alkyl) or --SR.sub.8 (wherein R.sub.8 is C.sub.1 -C.sub.4 alkyl); and Y.sub.3 is C.sub.1 -C.sub.5 alkyl, C.sub.2 -C.sub.8 alkenyl, halogen, --OR.sub.5 (wherein R.sub.5 is as defined above), --CO.sub.2 R.sub.6 (wherein R.sub.6 is as defined above), --N(R.sub.7).sub.2 (wherein R.sub.7 is as defined above) or --SR.sub.8 (wherein R.sub.8 is as defined above), or a pharmaceutically acceptable salt thereof.

Growing community of inventors

Funabashi, Japan

Ryozo Sakoda