Beta-lactam compounds and process for production thereof

Claim 2

A process for producing a compound of the general formula wherein R 1 represents a hydrogen atom, a methyl group, or a hydroxyl group, R 2 represents a hydrogen atom or an ester residue,'and R 51 representsaa monovalent organic group, or its salt, which comprises reacting a compound of the general formula wherein R 1 and R 2 are as defined above, or its salt, with a diazo compound of the formula wherein R 4 represents a divalent group remaining after removal of one hydrogen atom present on the carbon atom at the 1-position from a monovalent organic group in which the carbon atom at the 1-position is a primary or secondary carbon atom.

Claim 3

The process of claim 1 wherein the reaction is carried out at a temperature in the range of from about -50°C to about +50°C.

Claim 4

The process of claim 1 wherein the reaction is carried out at room temperature or at lower temperatures.

Claim 5

The process of claim 1 wherein the reaction is carried out in an inert organic solvent.

Claim 6

The process of claim 1 wherein the compound of formula (111-2) is used in an amount of at least 1 mole per mole of the compound of formula (II) or its salt.

Claim 7

The process of claim 1 wherein the compound of formula (111-2) is used in an amount of 1.1 to 2.0 moles per mole of the compound of formula (II) or its salt.

Claim 8

The process of claim 1 wherein said monovalent organic group has not more than 30 carbon atoms, preferably not more than 25 carbon atoms.

Claim 9

The process of claim 7 wherein said monovalent organic group is selected from the group consisting of (i) substituted or unsubstituted alkyl, alkenyl and alkynyl groups, (ii) cycloalkyl groups, (iii) cycloalkyl-alkyl groups, (iv) substituted or unsubstituted aryl groups, (v) substituted or unsubstituted aralkyl groups, (vi) heterocyclic groups, and (vii) heterocyclic-aralkyl groups.

Claim 10

The procdss of claim 1 wherein when R2 in formula (I-1) represents an ester residue easily splittable by hydrolysis or hydrogenolysis, the compound of formula (I-1) is subjected to sasponification or hydrogenolysis in a customary manner to form a compound of formula (I-1) wherein R 2 is a hydrogen atom or its salt.

Claim 11

A process for producing a compound of the general formula wherein R 1 represents a hydrogen atom, a methyl grour or a hydroxyl group, R 2 represents a hydrogen atom or an ester residue, and R 5 represents the group R 3 or -C0-R 3 in which R 3 represents a monovalent organic group, or its salt, which comprises reacting a compound of the general formula wherein R 2 is as defined above, or its salt, with a compound of the formula wherein R 3 is as defined above, and X represents a halogen atom or an activated carboxyl group.

Claim 12

A process for producing a compound of the general formula wherein R 1 represents a hydrogen atom, a methyl grour or a hydroxyl group, R 2 represents a hydrogen atom or an ester residue, and R 5 represents the group R 3 or -C0-R 3 in which R 3 represents a monovalent organic group, or its salt, which comprises reacting a compound of the general formula wherein R 2 is as defined above, or its salt, with a compound of the formula wherein R 3 is as defined above, and X represents a halogen atom or an activated carboxyl group.

Claim 13

The process of claim 10 wherein the reaction is carried out at a temperature in the range of from about -50°C to about +50°C.

Claim 14

The process of claim 10 wherein the reaction is carried out at room temperature or at lower temperatures.

Claim 15

The process of claim 10 wherein the compound of formula (II-1) or its salt is reacted in the presence of a base with the compound of formula (III-1) wherein X is a halogen atom.

Claim 16

The process of claim 10 wherein the reaction is carried out in an inert organic solvent.

Claim 17

The process of claim 10 wherein the compound of formula (III-1) is used in an amount of at least 1 mole per mole of the compound of formula (II-I) or its salt.

Claim 18

The process of claim 10 wherein the compound of formula (III-1) is used in an amount of 1.1 to 2.0 moles per mole of the compound of formula (II-I) or its salt.

Claim 19

The process of claim 10 wherein R 3 is a monovalent organic group having up to 30 carbon atoms, preferably up to 25 carbon atoms.

Claim 20

The process of claim 17 wherein the monovalent organic groups is selected from the class consisting of (i) substituted or unsubstituted alkyl, alkenyl and alkynyl groups, (ii) cycloalkyl groups, (iii) cycloalkyl-alkyl groups, (iv) substituted or unsubstituted aryl groups, (v) substituted or unsubstituted aralkyl groups, (vi) heterocyclic groups, and (vii) heterocyclic-alkyl groups.

Claim 21

19 . The process of claim 10 wherein wherein R 2 in formula (I) is an ester residue easily splittable by hydrolysis or hydrogenolysis, the compound of formula (I) is subjected to saponification or hydrogenolysis in a customary manner to form a compound of formula (I) in which R 2 is a hydrogen atom, or its salt.

Claim 22

A process for producing a compound of the general formula wherein R 1 represents a hydrogen atom, a methyl group, or a hydroxyl group and R 2 represents a hydrogen atom or an ester residue, which comprises reacting a compound of the general formula wherein Y represents an amino group which may be Protected, or its N-oxide-, or its salt, with a compound of the formula wherein M represents a hydrogen atom or an alkali metal.

Claim 23

A process for producing a compound of the general formula wherein R 1 represents a hydrogen atom, a methyl group, or a hydroxyl group and R 2 represents a hydrogen atom or an ester residue, which comprises reacting a compound of the general formula wherein Y represents an amino group which may be Protected, or its N-oxide-, or its salt, with a compound of the formula wherein M represents a hydrogen atom or an alkali metal.

Claim 24

The process of claim 20 wherein the reaction is carried out at room temperature or at lower temperatures.

Claim 25

The process of claim 21 wherein the reaction is carried out at a temperature in the range of from about - 30°C to about -50°C.

Claim 26

The process of claim 20 wherein the compound of formula (iv) or its salt is reacted in the presence of a base with the compound of formula (V) in which M is a hydrogen atom.

Claim 27

The process of claim 20 wherein the reaction is carried out in an inert organic solvent.

Claim 28

The process of claim 20 wherein the compound of formula (V) is used in an amount of at least 1 mole per mole of the compound of formula (IV) or its salt.

Claim 29

The process of claim 20 wherein the compound of formula (V) is used in an amount of 1.1 to 1.5 moles per mole of the compound of formula (IV) or its salt.

Claim 30

A compound of the general formula wherein R 2 represents a hydrogen atom or an ester residue, and R 51 represents (a) a hydrogen atom, (b) a lower alkyl group having a substituent selected from the class consisting of lower alkoxy, lower alkanoyloxy, amino, carbamoyl, carboxyl and substituted or unsubstituted benzyloxycarbonyl, (c) a pyridyl or thiazolyl group having a substituent selected from nitro, hydroxy, amino and N-oxide, or (d) a group of the formula -CO-R 6 , -CH 2 =R 7 , or -S-R 8 in which R 6 represents a lower alkyl group, a phenyl group which may be substituted, or a 5- or 6-membered heterocyclic group, R 7 represents a 5- or 6-membered heterocyclic group, and R 8 represents a group of the formula or a group of the formula -CH 2 CH 2 -Y in which Y represents an amino group which may be protected, or its N-oxide; or its salt.

Claim 31

A compound of the general formula wherein R 2 represents a hydrogen atom or an ester residue, and R 51 represents (a) a hydrogen atom, (b) a lower alkyl group having a substituent selected from the class consisting of lower alkoxy, lower alkanoyloxy, amino, carbamoyl, carboxyl and substituted or unsubstituted benzyloxycarbonyl, (c) a pyridyl or thiazolyl group having a substituent selected from nitro, hydroxy, amino and N-oxide, or (d) a group of the formula -CO-R 6 , -CH 2 =R 7 , or -S-R 8 in which R 6 represents a lower alkyl group, a phenyl group which may be substituted, or a 5- or 6-membered heterocyclic group, R 7 represents a 5- or 6-membered heterocyclic group, and R 8 represents a group of the formula or a group of the formula -CH 2 CH 2 -Y in which Y represents an amino group which may be protected, or its N-oxide; or its salt.

Claim 32

The compound or salt of claim 27 wherein R 51 represents (a) a hydroxyl group, (b) a lower alkyl group having 1 or 2 substituents selected from the class consisting of methoxy, ethox y , acetyloxy, propionyloxy, amino, carbamoyl, carboxy-and the group in which R 16 represents a hydrogen atom, a lower alkoxy group, a lower alkyl group or a nitro group, (c) a pyridyl or thiazolyl group having one substituent selected from the class consisting of nitro, hydroxy, amino and N-oxide, or (d) a group of the formula -CO-R 61 , CH 2 -R 71 or -S-R 81 in which R 61 represents a lower alkyl group, the group in which R 17 represents a lower alkyl group, a lower alkoxy group, a nitro group, a hydroxyl group, an amino group, or a halogen atom, or a 5- or 6-membered heterocyclic group having 1 or 2 nitrogen atoms and which may be mono-substituted with halogen, lower alkyl, lower alkoxy, amino, cyano, nitro, hydroxy or N-oxide, R 71 represents a 5- or 6-membered heterocyclic group having 1 or 2 nitrogen atoms and which may be mono-substituted by halogen, lower alkyl, lower alkoxy, amino, cyano, nitro, hydroxyl or N-oxide, and R 81 represents a group of the formula or the group -CH 2 CF-Y' in which Y' represents an amino, group, an acetylamino group, or its oxide.

Claim 33

The compound or its salt of claim 27 or 28 wherein R 2 represents a lower alkyl group, a p-nitrobenzyl group, or a pivaloyloxymethyl group.