"Triazolo-pyrimidine intermediates"

• US 4,956,462 A
• Filed: 05/26/1989
• Issued: 09/11/1990
• Est. Priority Date: 08/07/1987
• Status: Expired due to Fees

• Current Assignee: Nippon Pharmaceutical Development Institute Company Limited, Sankei Pharmaceutical Company Limited
• Original Assignee: Nippon Pharmaceutical Development Institute Company Limited, Sankei Pharmaceutical Company Limited
• Inventors: Shimizu, Shigeo, Takano, Hiroyuki
• Primary Examiner(s): RIZZO, NICHOLAS
• Application Number:
  US07/357,124
• Time in Patent Office: 473 Days
• Field of Search: 544/262, 544/263, 544/281, 544/280
• US Class Current: 544/263
• CPC Class Codes: C07D 519/00 Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

There are disclosed a β-lactam compound represented by the formula (I): ##STR1## wherein R₁ represents an acyl group; M represents a hydrogen atom, a protective group of an eliminatable group which is easily hydrolyzable in a human body; B represents a group represented by the formula (b): ##STR2## where at least one of R₂, R₃ and R₉ represent a group represented by the formula: -A-OR₄ where R₄ represents a hydrogen or a lower alkyl group; and A represents a straight or branched alkylene group having 1 to 6 carbon atoms; and a remaining group or groups are each independently a hydrogen atom; a cyano group; a lower alkyl group which may be substituted by a halogen atom; a carbamoyl group which may be substituted by a lower alkyl group; a cycloalkyl group; or a carboxyl group which may be substituted by a protective group of an eliminatable group which is easily hydrolyzable in a human body, and also when R₉ is -A-OR₄, R₂ and R₃ may be combined with each other to form an alkylene group having 3 to 4 carbon atoms; and Z represents a nitrogen atom or a group represented by the formula: C-R₁₀ where R₁₀ represents a hydrogen atom, a carboxyl group or a lower alkyl group which may be substituted by a hydroxy group or a lower alkoxy group,

or its pharmaceutically acceptable salt, and a process for preparing the same, an intermediate for synthesis of the same and a medicinal composition for bacterially infectious disease therapy containing the same.

Claims

1. A compound represented by the formula (VII'"'"'):

##STR23## where at least one of R₂, R₃ and R₉ represent a group represented by the formula;

--A--OR₄ where R₄ represents a hydrogen or a lower alkyl group; and

A represents a straight or branched alkylene group having 1 to 6 carbon atoms; and

a remaining group or groups are each independently a hydrogen atom;

a cyano group;

a lower alkyl group which may be substituted by a halogen atom;

a carbamoyl group which may be substituted by a lower alkyl group;

a cycloalkyl group;

or a carboxyl group which may be substituted by a protective group or an eliminatable group which is easily hydrolyzable in a human body, and also when R₉ is --A--OR₄, R₂ and R₃ may be combined with each other to form an alkylene group having 3 to 4 carbon atoms;

Z represents a nitrogen atom or a group represented by the formula;

C--R₁₀ where R₁₀ represents a hydrogen atom, a carboxyl group or a lower alkyl group which may be substituted by a hydroxy group or a lower alkoxy group; and

X represents a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom.

2. A compound according to claim 1, wherein the protective group is selected from the group consisting of a diphenylmethyl group, a t-butyl group, a p-nitrobenzyl group and a trimethylsilyl group and the eliminatable group which is easily hydrolyzable in a human body is selected from the group consisting of an acetoxymethyl group, an α

-acetoxyethyl group, a pivaroyloxymethyl group, an ethoxycarbonyloxymethyl group, an α

-methoxycarbonyloxymethyl group, an α

-methoxycarbonyloxyethyl group, an α

- ethoxycarbonyloxyethyl group, a 1-indanyl, a phthalidyl group, and a 5-methyl-2-oxo-1,3-dioxol-4-yl-methyl group.

3. A compound according to claim 2, wherein the cycloalkyl group is selected from the group consisting of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group.