Shionogi Company Limited

Tatsuo Tsuri

Mitsuaki Ohtani

Nobuhiro Haga

Susumu Kamata

Kaoru Seno

Fumihiko Watanabe

Tsunetoshi Honma

Akinori Arimura

Sanji Hagishita

Kenji Kawada

Tadahiko Tsushima

Junji Kishino

Masayuki Narisada

Kimio Takahashi

Morio Kishi

Takeaki Matsui

Masanao Inagaki

Saichi Matsumoto

Hirokuni Jyoyama

Sanji Hagashita

Bicyclic amino derivatives and PGD2 antagonist containing the same

Bicyclic amino derivatives and PGD2, antagonist containing them

Benzylidene derivatives having anti-inflammatory activities, are shown by the following formula I: ##STR1## wherein A is -CH.sub.2 - or -CH.sub.2 CH.sub.2 -; B is a bond or -CH.sub.2 -, -CHOH-, -CO-, -O-, or A and B may taken together form -CH=CH-; D is &gt;N- or &gt;CH-; R.sup.1 and R.sup.2 each independently is hydrogen, lower alkyl or lower alkoxy; R.sup.3 is hydrogen, lower alkyl, cycloalkyl, lower alkoxy, arylalkyloxy, heteroarylalkyloxy, lower alkylcarbonyl, arylcarbonyl, substituted or unsubstituted carbamoyl, or a group of the formula:

Benzylidene derivatives

Lipid derivatives represented by the formula: ##STR1## wherein R.sub.1 is alkyl or alkylcarbamoyl; R.sub.2 is lower alkyloxy, lower alkylcarbamoyloxy, lower alkylcarbonylamino, lower alkyloxycarbonylamino, lower alkylureido, lower alkyloxymethyl, lower alkylcarbonylmethyl, cyanomethyl, heterocyclic group, or heterocyclyloxy; R.sub.2 ' is hydrogen or R.sub.2 and R.sub.2 ' taken together with R.sub.2 form --O(CH.sub.2).sub.m -- wherein m is an integer of 1 to 5; R.sub.3, R.sub.4, and R.sub.5 each is hydrogen or lower alkyl or two or three of R.sub.3, R.sub.4, and R.sub.5 taken together with the adjacent nitrogen atom form cyclic ammonio; R.sub.6 is hydrogen or lower alkylcarbonyl; X.sup.- is a counter anion; Y is oxygen or sulfur; and n is an integer of 1 to 10, being useful as PAF antagonists, e.g., as antithrombotic, antivasoconstricting, antibronchoconstricting agent or antitumor agent.

Lipid derivatives

Lipid derivatives represented by the formula: ##STR1## wherein R.sub.1 is alkyl or alkylcarbamoyl; R.sub.2 is lower alkyloxy, lower alkylcarbamoyloxy, lower alkylcarbonylamino, lower alkyloxycarbonylamino, lower alkylureido, lower alkyloxymethyl, lower alkylcarbonylmethyl, cyanomethyl, heterocyclic group, or he0 terocyclyloxy; R.sub.2 ' is hydrogen or R.sub.2 and R.sub.2 ' taken together form --O(CH.sub.2).sub.m -- wherein m is an integer of 1 to 5; R.sub.3, R.sub.4, and R.sub.5 each is hydrogen or lower alkyl or two or three of R.sub.3, R.sub.4, and R.sub.5 taken together with the adjacent nitrogen atom form cyclic ammonio; R.sub.6 is hydrogen or lower alkylcarbonyl; X.sup.- is a counter anion; Y is oxygen or sulfur; and n is an integer of 1 to 10, being useful as PAF antagonists, e.g., as antithrombotic, antivasoconstricting, antibronchoconstricting agent or antitumor agent.

There are provided compounds of the formula: ##STR1## wherein R.sub.1 is a hydrogen or C.sub.1 -C.sub.5 alkyl; R.sub.2 is an C.sub.1 -C.sub.10 alkyl, aryl, aralkyl, or pyridyl, where the aryl, aralkyl, or pyridyl are unsubstituted or are substituted by C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, hydroxy, carboxy, amino, C.sub.1 -C.sub.5 alkylamino, C.sub.1 -C.sub.5 dialkyamino whose two alkyl groups may be different from each other, C.sub.2 -C.sub.3 alkanoylamino, or halogen and X is an C.sub.1 -C.sub.7 alkylene, C.sub.2 -C.sub.7 alkenylene, --CH(F)CH.dbd.CH(CH.sub.2).sub.3 --, --(CH.sub.2).sub.3 --S--(CH.sub.2).sub.2 --, --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.3 --, --C.sub.6 H.sub.4 -O--CH.sub.2 -- or --CH.sub.2 CH.dbd.CH--m--C.sub.6 H.sub.4 --, or their pharmaceutically accepatble salts. The compounds are useful as antithrombotic, anti-vasconstricting and anti-bronchoconstricting drugs.

6-oxa and thiabicyclo [3.1.0.] compounds

Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or hetelocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms and may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.

7-oxabicyclo[2.2.1] heptane sulfonamide derivatives

Bicyclic sulfonamido derivatives represented by the formula: ##STR1## wherein R.sub.1 is a hydrogen or lower alkyl; R.sub.2 is an alkyl, substituted or unsubstituted aryl, aralkyl or heterocycle; R.sub.3 is a hydrogen or methyl; X is an alkylene or alkenylene which may be substituted by a fluorine atom or atoms an may contain an oxygen, sulfur and/or phenylene in the chain; Y is straight or branched alkylene or alkenylene, oxygen, or sulfur; m is 0 or 1; and n is 0, 1 or 2, or their salt, said derivatives being useful as antithrombotic, anti-vasoconstricting, and anti-bronchoconstricting drugs.

Bicyclic sulfonamide derivatives

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Kobe, Japan

Tatsuo Tsuri