KR880003956A - New Cephalosporin Compounds - Google Patents

Abstract

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Description

New Cephalosporin Compounds

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Claims (13)

Compounds of the following general formula (I) and salts and solvates thereof (including hydrates). Wherein R ¹ and R ² may be the same or different from each other, and are each a hydrogen atom or a carboxyl blocking group, R ³ is a hydrogen atom or an amino protecting group, and R ⁴ and R ⁵ are each a hydroxy or substituted hydroxy group Or R ⁴ and R ⁵ together are a cyclic protective diol group, Z is -S- or -SO-, and the 2-, 3- and 4-positions linked with a dotted line indicate that the compound is cef-2-em or cef. 3-M compound. The compound of formula (Ia) and nontoxic salts, solvates (including hydrates) and metabolically labile esters of claim 1. In the above formula, R ^4a is hydroxy or ecetoxy, and R ^5a is a hydroxyl group or an acetoxy group. The compound of formula (Ia) according to claim 2, wherein the oxime etherification group has an S-configuration. (6R, 7R, 2'Z, S) -7- [2- (2-aminothiazol-4-yl) -2-[(carboxy) (3,4-dihydroxyphenyl) methoxyimino] acet Amido] sef-3-em-4-carboxylic acid, and its nontoxic salts, solvates (including hydrates) and metabolically labile esters. The compound of claim 4 which is in crystalline hydration type. Includes absorption bands at 3700-2100 (Brodo), 1760, 1720, 1660, 1555, 1520, 1350, 1300, 1290, 1240, 1215, 1170, 1155, 1120, 1030, 1000, 920, 860 and 755 cm ^-1 The crystalline hydration compound of claim 5, characterized by an infrared spectrum. The crystalline hydration compound of claim 5, characterized by the following X-ray diffraction pattern (expressed in d plane spacing and percent intensity in Angstrom units). 12.5 (21): 9.97 (37): 9.51 (22): 6.79 (11): 6.33 (35): 5.29 (10): 4.76 (30): 4.63 (100): 4.39 (54): 4.32 (5): 4.18 (15): 4.09 (31): 3.91 (24): 3.78 (69): 3.69 (17): 3.61 (9): 3.52 (12): 3.48 (21): 3.42 (6): 3.33 (37): 3.15 (36): 3.07 (22): 3.02 (4): 2.96 (36): 2.85 (9): 2.78 (3): 2.75 (3): 2.65 (11): 2.59 (49): 2.50 (6): 2.44 (9): 2.38 (6): 2.31 (3): 2.27 (4): 2.20 (5): 2.16 (9): 2.10 (10): 2.05 (4): 2.01 (9) Compounds of the general formula (II) or salts thereof or 7-N-silyl derivatives thereof are acylated using the compounds of the general formula (III) or salts thereof or the corresponding acylating agents, and then Depending on the purpose, any reaction as follows: i) converting the Δ ² -isomer to the desired Δ ³ -isomer, and ii) reducing the compound with Z of -SO- to produce a compound with Z of -S- Iii) converting the carboxyl group to a metabolically labile nontoxic ester functional group, iii) producing a nontoxic salt or solvate, iii) removing any carboxyl blocking group and / or N-protecting group, and iii) any A method for producing a compound of formula (I) or a salt or solvate thereof as defined in claim 1, wherein the reaction for removing the hydroxy blocker is carried out in a suitable order. In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Z and the dotted line are as defined in claim 1. (6R, 7R, 2'Z, S) -7- [2- (2-aminothiazol-4-yl) -2-[(carboxy) (3,4-dihydroxyphenyl) methoxyimino] acet A method for producing the crystalline hydrate of claim 5, wherein an aqueous solution of amido] sep-3-em-4-carboxylic acid, or acid addition salts or base salts or solvates thereof is formed and crystallized therefrom. . (6R, 7R, 2'Z, S) -7- [2- (2-aminothiazol-4-yl) -2-[(carboxy) (3,4-dihydroxyphenyl) methoxyimino] acet Preparation of the crystalline hydrate of claim 5, wherein an acid addition salt or a base salt of amido] se-3-em-4-carboxylic acid or an aqueous solution of a solvate thereof is produced and the pH of the solution is adjusted to 1.0 to 4.0. Way. A pharmaceutical composition comprising the compound of formula (Ia) as defined in claim 2 as an active ingredient. The pharmaceutical composition of claim 11, wherein the active ingredient is a compound as defined in claim 4. The pharmaceutical composition according to claim 12, wherein the active ingredient is the crystalline hydration compound of claim 5. ※ Note: The disclosure is based on the initial application.