Yamanouchi Pharmaceutical Company Ltd.

Kuniichiro Yano

Masuo Murakami

Tadao Shibanuma

Masaru Iwanami

Masaharu Fujimoto

Ryutaro Kawai

Norio Sato

Yukiyasu Murakami

Akio Koda

Ichiro Isaka

Kohzi Nakano

Norio Kawahara

Teruya Ashiwagi

Isao Souzo

N-alkenyltetracycline derivatives, for example, N-(1-methyl-2-.alpha.-naphthylethenyl)tetracycline represented by the formula ##SPC1## The compounds have excellent antibacterial action as compared with tetracycline.

N-alkenyltetracycline derivatives

The ampicillin derivatives represented by the general formula ##SPC1## Wherein R represents ##SPC2## Wherein R' represents a hydrogen atom, a methyl group, or an ethyl group and A and B each represents a hydrogen atom, a hydroxyl group, a methyl group, a methoxy group, a nitro group, or a halogen atom and further said B may combine with A on the carbon atom at the position to form ##SPC3## Group (where in Z represents --CH=N-- or --CH=CH-- and an R.sup.2 represents a hydrogen atom, a hydroxyl group, a phenyl group, a methyl group, an ethyl group, a methoxy group, an ethoxyl group, a methylthio group, a trifluoromethyl group, a halogen atom, a nitro group, an acetyl group, an acetamido group, a ethoxycarbonyloxy group, or a methylsulfonyl group and further R.sub.2 and ##SPC4## May form a thiazole, isothiazolo, pyrrolo, furo, or benzo fused ring which may be substituted by an oxo group, a methyl group, or an acetyl group) and the dotted line means an arbitrary double bond, ##SPC5## Wherein R.sup.3 and R.sup.4 each represents a hydrogen atom or a methyl group, ##SPC6## Wherein R.sup.5 represents a halogen atom, a methoxy group, a nitro group, or a hydroxyl group and R.sup.6 represents a hydrogen atom, a methoxy group, a halogen atom, a nitro group, or a hydroxyl group, or ##SPC7## Wherein R.sup.7 represents a hydrogen atom or a hydroxyl group, Y represents O or S, and the dotted line means an arbitrary double bond, said substituent group, being bonded to the ampicillin molecule through --CO-- at the 2-position, 3-position, 5-position or 6-position when the oxo group (+0) is at the 4-portion and being bonded to the ampicillin molecule through the --CO-- group at the 2-position, 4-position, or 5-position when the oxy group is at the 6-position, and salts of the ampicillin derivatives. Those compounds are valuable as antibacterial agents.

Ampicillin derivatives substituted by heterocyclic acyl group

N-alkenyltetracycline derivatives, for example, N-[1-methyl-2(2-thienyl)-1-butenyl]tetracycline represented by the formula ##SPC1## The compounds have excellent antibacterial action as compared with tetracycline.

Novel N-alkenyltetracycline derivatives

Growing community of inventors

Tokorozawa, Japan

Kuniichiro Yano