EP0333154A2 — Process for the preparation of cephem derivatives…

Claim 1

Independent Claim 129 words

A process for the preparation of a cephem derivative represented by the following formula: wherein R₁ means a fluorine-substituted lower alkyl and A₁ denotes a cyclic or acyclic ammonio group, or a non-toxic salt thereof, which comprises reacting a compound represented by the following formula: wherein A₁ has the same meaning as defined above, a compound obtained by blocking the -COO⁻ of said another compound with a protecting group, or a salt thereof, with another compound represented by the following formula: wherein R₁ has the same meaning as defined above, a compound obtained by blocking the amino group of the first-mentioned compound with a protecting group, a reactive derivative of the first-mentioned compound at the carboxyl group thereof, or a salt thereof and if necessary, removing the protecting groups.

Claim 2

Dependent Claim 129 words

A process for the preparation of a cephem derivative represented by the following formula: wherein R₁ means a fluorine-substituted lower alkyl and A₁ denotes a cyclic or acyclic ammonio group, or a non-toxic salt thereof, which comprises reacting a compound represented by the following formula: wherein A₁ has the same meaning as defined above, a compound obtained by blocking the -COO⁻ of said another compound with a protecting group, or a salt thereof, with another compound represented by the following formula: wherein R₁ has the same meaning as defined above, a compound obtained by blocking the amino group of the first-mentioned compound with a protecting group, a reactive derivative of the first-mentioned compound at the carboxyl group thereof, or a salt thereof and if necessary, removing the protecting groups.

Claim 3

Dependent Claim 29 words

A cephem derivative represented by the following formula: wherein R₁ means a fluorine-substituted lower alkyl and A₁ denotes a cyclic or acyclic ammonio group, or a non-toxic salt thereof.

Claim 4

Dependent Claim 29 words

A cephem derivative represented by the following formula: wherein R₁ means a fluorine-substituted lower alkyl and A₁ denotes a cyclic or acyclic ammonio group, or a non-toxic salt thereof.

Claim 5

Dependent Claim 6 words

7β-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-(Z)-2-fluoromethoxyiminoacetamido]-3-(E)-3-[((R)-1-carbamoyl-2-hydroxyethyl)dimethylammonio]-1-propenyl]-3-cephem-4-carboxylate, as claimed in Claim 2.

Claim 6

Dependent Claim 8 words

7β-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-(Z)-2-fluoromethoxyiminoacetamido]-3-[(E)-3-(carbamoylmethyl ethylmethylammonio)-1-propenyl] -3-cephem-4-carboxylate, as claimed in Claim 2.

Claim 7

Dependent Claim 81 words

A compound represented by the following formula: wherein R₆ means an amino group or an amino group blocked by a protecting group, and A₂ denotes a group represented by the following formula: all R₇ being either the same or different and meaning individually a lower alkyl group and R₈ denoting a lower alkyl group substituted by a hydroxyl group and/or a carbamoyl group, a compound obtained by blocking -COO⁻ of the first-mentioned compound with a protecting group, or a salt thereof.

Claim 8

Dependent Claim 81 words

A compound represented by the following formula: wherein R₆ means an amino group or an amino group blocked by a protecting group, and A₂ denotes a group represented by the following formula: all R₇ being either the same or different and meaning individually a lower alkyl group and R₈ denoting a lower alkyl group substituted by a hydroxyl group and/or a carbamoyl group, a compound obtained by blocking -COO⁻ of the first-mentioned compound with a protecting group, or a salt thereof.

Claim 9

Dependent Claim 4 words

7β-Amino-3-[(E)-3-[((R)-1-carbamoyl-2-hydroxyethyl)dimethylammonio]-1-propenyl]-3-cephem-4-carboxylate or perchlorate thereof.

Claim 10

Dependent Claim 4 words

7β-Amino-3-[(E)-3-[((R)-1-carbamoyl-2-hydroxyethyl)dimethylammonio]-1-propenyl]-3-cephem-4-carboxylate or perchlorate thereof.

Claim 11

Dependent Claim 4 words

7β-Amino-3-[(E)-3-(carbamoylmethylethylmethylammonio)-1-propenyl]-3-cephem-4-carboxylate or paratoluenesulfonate thereof.

Claim 12

Dependent Claim 4 words

7β-Amino-3-[(E)-3-(carbamoylmethylethylmethylammonio)-1-propenyl]-3-cephem-4-carboxylate or paratoluenesulfonate thereof.

Claim 13

Dependent Claim 149 words

A process for the preparation of a compound represented by the following formula: wherein R₆ means an amino group or an amino group blocked with a protecting group, and A₂ denotes a group represented by the following formula: all R₇ being either the same or different and meaning individually a lower alkyl group and R₈ denoting a lower alkyl group substituted by a hydroxyl group and/or a carbamoyl group, a compound obtained by blocking -COO⁻ of the first-mentioned compound with a protecting group, or a salt thereof, which comprises reacting a compound represented by the following formula: wherein R₆ has the same meaning as defined above and X denotes a halogen atom, a compound obtained by blocking the carboxyl group of the last-mentioned compound with a protecting group or a salt thereof with an amine corresponding to A₂ or a salt thereof; and if necessary, removing the protecting group.

Claim 14

Dependent Claim 149 words

A process for the preparation of a compound represented by the following formula: wherein R₆ means an amino group or an amino group blocked with a protecting group, and A₂ denotes a group represented by the following formula: all R₇ being either the same or different and meaning individually a lower alkyl group and R₈ denoting a lower alkyl group substituted by a hydroxyl group and/or a carbamoyl group, a compound obtained by blocking -COO⁻ of the first-mentioned compound with a protecting group, or a salt thereof, which comprises reacting a compound represented by the following formula: wherein R₆ has the same meaning as defined above and X denotes a halogen atom, a compound obtained by blocking the carboxyl group of the last-mentioned compound with a protecting group or a salt thereof with an amine corresponding to A₂ or a salt thereof; and if necessary, removing the protecting group.

Claim 15

Dependent Claim 11 words

A compound represented by the following formula: or a salt thereof.

Claim 16

Dependent Claim 11 words

A compound represented by the following formula: or a salt thereof.

Claim 17

Dependent Claim 11 words

A compound represented by the following formula: or a salt thereof.

Claim 18

Dependent Claim 11 words

A compound represented by the following formula: or a salt thereof.

Claim 19

Dependent Claim 18 words

A compound represented by the following formula: wherein R₇ means a lower alkyl group, or a salt thereof.

Claim 20

Dependent Claim 18 words

A compound represented by the following formula: wherein R₇ means a lower alkyl group, or a salt thereof.

Claim 21

Dependent Claim 22 words

Pharmaceutical composition containing at least one compound or a pharmaceutically acceptable salt thereof according to any of claims 2, 3 or 4.

Claim 22

Dependent Claim 25 words

The use of compounds according to any of claims 2, 3 or 4 or their pharmaceutically acceptable salts for the making of an antibacterial medicament.

Claim 23

Dependent Claim 28 words

The use of compounds according to any of the preceding claims 5, 6 or 7 or 9, 10 or 11 for the manufacture of compounds of claim 2.

Process for the preparation of cephem derivatives and intermediates therefor

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