7-Acylamino-3-vinylcephalosporanic acid derivatives and processes for the preparation thereof

• US 4,409,214 A
• Filed: 11/10/1980
• Issued: 10/11/1983
• Est. Priority Date: 11/19/1979
• Status: Expired due to Term

• Current Assignee: Fujisawa Pharmaceutical Co., Ltd. (Astellas Pharma Incorporated)
• Original Assignee: Fujisawa Pharmaceutical Co., Ltd. (Astellas Pharma Incorporated)
• Inventors: Yamanaka, Hideaki, Takasugi, Hisashi, Kawabata, Kohji, Takaya, Takao, Masugi, Takashi
• Primary Examiner(s): Chan, Nicky
• Application Number:
  US06/205,334
• Time in Patent Office: 1,065 Days
• Field of Search: 544/22, 544/29, 544/23, 424/246
• US Class Current: 514/202
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: C07D 209/48 with oxygen atoms in positions 1 and 3, e.g. phthalimide
• CPC Class Codes: C07D 213/75 Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30
• CPC Class Codes: C07D 257/06 with nitrogen atoms directly attached to the ring carbon atom
• CPC Class Codes: C07D 271/06 1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
• CPC Class Codes: C07D 271/07 with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 277/20 having two or three double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 277/46 by carboxylic acids, or sulfur or nitrogen analogues thereof
• CPC Class Codes: C07D 277/48 by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
• CPC Class Codes: C07D 277/56 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• CPC Class Codes: C07D 277/587 with aliphatic hydrocarbon radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom
• CPC Class Codes: C07D 285/08 1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

This invention relates to novel 7-acylamino-3-vinyl-cephalosporanic acid derivatives and pharmaceutically acceptable salts thereof, of high antimicrobial activity.

Claims

1. A compound of the formula:

##STR26## in which R¹ is 2-aminothiazol-4-yl or 2-acylaminothiazol-4-yl,

R² is carboxy or a protected carboxy group, and

R⁴ is lower alkyl substituted by carboxy or a protected carboxy group,

and a pharmaceutically acceptable salt thereof.

2. A compound of claim 1, in which

R² is carboxy.

3. A compound of claim 2, in which

R⁴ is carboxy(lower)alkyl.

4. A compound of claim 3, in which

R¹ is 2-aminothiazol-4-yl.

5. A compound of claim 4, which is

7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid or its hydrochloride or its disodium salt.

6. A compound of claim 4, which is

trihydrate of 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid.

7. A compound of claim 1, in which

R² is mono- or di- or triphenyl(lower)alkoxycarbonyl, or lower alkanoyloxy(lower)alkoxycarbonyl.

8. A compound of claim 7, in which

R⁴ is lower alkanoyloxy(lower)alkoxycarbonyl(lower)alkyl or lower alkoxycarbonyl(lower)alkyl.

9. A compound of claim 8, in which

R¹ is 2-aminothiazol-4-yl.

10. A compound of claim 9, which is

pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-pivaloyloxymethoxycarbonylmethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylate.

11. An antimicrobial pharmaceutical composition comprising, as active ingredients, an effective amount of the compound claimed in claim 1, in admixture with pharmaceutically acceptable carriers.

12. A method for treating an infectious disease caused by pathogenic microorganisms, which comprises administering a compound claimed in claim 1 to infected human beings or animals.