Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1988-10-13
1992-01-28
Rizzo, Nicholas S.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
540225, 540227, 540222, 514206, C07D50122, A61K 31545
Patent
active
050844539
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel cephalosporin derivatives, a process for their production, antibacterial agents containing them as active ingredients and intermediates for their production.
BACKGROUND TECHNOLOGY
Heretofore, a number of compounds have been synthesized which have a 2-substituted oxyiminoacetamide group as a side chain at the 7-position of the cephem nucleus. For example, there may be mentioned a 2-(2-aminothiazol-4-yl)-2-substitued oxyiminoacetamide group, a 2-(2-aminoxazol-4-yl)-2-substituted oxyiminoacetamide group, a 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-substituted oxyiminoacetamide group, a 2-(furyl-2-yl)-2-substituted oxyiminoacetamide group or a 2-substituted phenyl-2-substituted oxyiminoacetamide group. As publications which disclose such compounds, for example, Japanese Unexamined Patent Publications No. 52083/1975, No. 102293/1977, No. 116492/1977, No. 137988/1978, No. 154786/1979, No. 157596/1979, No. 154980/1980, No. 86187/1981, No. 59895/1982, No. 99592/1982, No. 158769/1982, No. 192394/1982, No. 8087/1983 and No. 174387/1983, and The Chemical Society of Japan, Vol. 5, p.785-805 (1981), may be mentioned. It is disclosed that such compounds exhibit antibacterial activities against Gram-positive bacteria and Gram-negative bacteria including Pseudomonas aeruginosa thus suggesting that they have excellent antibacterial activities and a broad antibacterial spectrum.
In addition to the above publications, as the prior arts concerning the present invention, Japanese Unexamined Patent Publications No. 9296/1979, No. 162592/1983, No. 108792/1984, No. 130294/1984, No. 34972/1985, No. 67483/1985 and No. 97982/1985, may be mentioned. In the claims of such publications, as substituents of the 2-(2-aminothiazol-4-yl)-2-substituted oxyiminoacetamide group at the 7-position of the cephem nucleus, a number of substituents are mentioned including an alkyl group and an alkenyl group. Further, the description of the alkenyl group is general referring, for example, to an alkenyl group which may be substituted, or a substituted unsubstituted C.sub.2 -C.sub.8 alkenyl group. However, the alkenyl group suggested by the specific disclosure and examples in the specifications is an unsubstituted alkenyl group such as a vinyl group or an allyl group. Further, as the alkenyl group substituted by a carboxyl group, there is only a 1-carboxylate allyl group, and there is no disclosure or suggestion concerning the 1-carboxy-1-vinyl group in the above prior art references. Further, with respect to the prior art relating to intermediates, a number of 2-substituted oxyiminoacetic acid derivatives have been synthesized as the acyl side chain acid at the 7-position of the cephem nucleus. As such an acyl side chain acid, for example, a 2-(2-aminothiazol-4-yl)-2-substituted oxyiminoacetic acid, a 2-(thiazol-4-yl)-2-substituted oxyiminoacetic acid, a 2-(2-aminooxazol-4-yl)-2-substituted oxyiminoacetic acid, a 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-substituted oxyiminoacetic acid a 2-(furyl-2-yl)-2-substituted oxyiminoacetic acid or a 2-(substituted phenyl)-2-substituted oxyiminoacetic acid, may be mentioned. As the publications describing such 2-substituted oxyiminoacetic acid compounds, for example, Journal of the Japanese Chemical Society, p.785-804 (1981), the J. of Antibiotics, Vol. 34, p.1447-1455 (1981), ditto Vol. 35, p.712-720 (1982), ditto Vol. 36, p.1205-1210 (1983), ditto Vol. 37, p.532-571 (1984) and ditto Vol. 39, p.111-127 and p.404-414 ( 1986) may be mentioned. As the substituents of such substituted oxyimino groups, for example, lower alkyl, lower alkenyl, lower alkynyl, aralkyl and aryl groups which may have one or more substituents such as a hydroxyl group, a carboxyl group, a carbamoyl group, a cyano group, an amino group, a halogen atom, an alkyl group and an aryl group, are generally known.
Further, a 2-(1-vinyloxyimino)acetic acid derivative having a vinyl group as a substituent of the substituted oxyimino group is described in Japanese Unexamined Patent Publication No. 22392/
REFERENCES:
patent: 4196205 (1980-04-01), Deymes et al.
patent: 4464368 (1984-08-01), O'Callaghan et al.
patent: 4959469 (1990-09-01), Nakagawa et al.
Chemical Abstracts, vol. 110, 75154(b) (1989) Abstracting Oct WO87/06232, Apr. 14, 1986.
Asai Akira
Ishikawa Moriaki
Kuroyanagi Satoru
Mitomo Ryuji
Nakagawa Susumu
Banyu Pharmaceutical Co. Ltd.
Rizzo Nicholas S.
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