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US4263292A Expired / Lapsed US ⏱️ 0.0 years remaining

7α-methoxycephalosporins and pharmaceutical composition comprising the same

Assignee: Toyama Chemical Co Ltd
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Filing: 1979-10-04
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Granted: 1981-04-21
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Expires: 1999-10-04
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Abstract

Abstract A 7 alpha -methoxycephalosporin represented by the general formula and a salt thereof: <IMAGE> wherein R1 represents a hydrogen atom or a carboxyl-protecting group; R2 represents an organic group linked to the carbon atoms through an oxygen or sulfur atom; R3 represents a lower alkyl group; n is 0, 1 or 2; A represents a hydrogen atom or a substituted or unsubstituted alkyl group; and B represents a substituted or unsubstituted alkyl group. These compounds have a broad antibacterial spectrum and high resistance to beta -lactamase produced from bacteria, and are well absorbed in a living body.

Inventors

  • 👤 Isamu Saikawa
  • 👤 Shuntaro Takano
  • 👤 Hiroyuki Imaizumi
  • 👤 Isamu Takakura
  • 👤 Hirokazu Ochiai
  • 👤 Takashi Yasuda
  • 👤 Hideo Taki
  • 👤 Masaru Tai
  • 👤 Yutaka Kodama

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-24 20:07
CPC Classifications
C; C07; C07D; C07D241/00; C07D241/02; C07D241/06; C07D241/08; C07D295/00; C07D295/16; C07D295/20; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 27
Claim 1
Independent Claim 271 words
A 7α-methoxycephalosporin or salt thereof, said 7α-methoxycephalosporin being represented by the formula: ##STR41## wherein R' represents a hydrogen atom or a carboxyl-protecting group; R 2 represents a substituted or unsubstituted lower alkoxy, lower alkylthio, C 1-10 acyloxy, carbamoyloxy or heterocyclic thio group in which the thio linkage is attached to a carbon atom of a 5 or 6 membered aromatic heterocyclic ring composed of carbon and at least one hetero atom selected from oxygen, sulfur and nitrogen, the heterocyclic moiety of said heterocyclic thio group being composed of said aromatic heterocyclic ring or of said aromatic heterocyclic ring fused to a benzene ring or being triazolopyridyl, purinyl, or pyridine-1-oxide-2-yl, the substituent of the substituted group being selected from a halogen, lower alkyl, phenyl, C 2-5 alkenyl, hydroxyl, lower alkoxy, lower alkylthio, nitro, cyano, lower alkylamino, di-lower alkylamino, C 1-10 acylamino, C 1-10 acyl, C 1-10 acyloxy, C 1-10 acyl-lower alkyl, carboxyl, carbamoyl, amino-lower alkyl, N-lower alkylamino-lower alkyl, N,N-di-lower alkyl-amino-lower alkyl, hydroxy-lower alkyl, hydroxyimino-lower alkyl, lower alkoxy-lower alkyl, carboxy-lower alkyl, sulfo-lower alkyl, sulfo, sulfamoyl-lower alkyl, sulfamoyl, carbamoyl-lower alkyl, carbamoyl-C 2-5 alkenyl, and N-hydroxycarbamoyl-lower alkyl; R 3 represents a lower alkyl group; n is 0, 1 or 2; A represents a hydrogen atom or a straight- or branched-chain C 1-14 alkyl group which is unsubstituted or substituted with a halogen, lower alkoxy, cyano, nitro, carboxyl, lower alkoxycarbonyl, hydroxyl, lower alkylthio or C 1-10 acyl group; and B represents a straight- or branched-chain C 1-14 alkyl group which is unsubstituted or substituted with a halogen, hydroxyl, protected hydroxyl, C 1-10 acyl, mercapto, lower alkylthio, nitro, amino, protected amino, imino, protected imino or carboxyl group.
Claim 2
Dependent Claim 271 words
A 7α-methoxycephalosporin or salt thereof, said 7α-methoxycephalosporin being represented by the formula: ##STR41## wherein R' represents a hydrogen atom or a carboxyl-protecting group; R 2 represents a substituted or unsubstituted lower alkoxy, lower alkylthio, C 1-10 acyloxy, carbamoyloxy or heterocyclic thio group in which the thio linkage is attached to a carbon atom of a 5 or 6 membered aromatic heterocyclic ring composed of carbon and at least one hetero atom selected from oxygen, sulfur and nitrogen, the heterocyclic moiety of said heterocyclic thio group being composed of said aromatic heterocyclic ring or of said aromatic heterocyclic ring fused to a benzene ring or being triazolopyridyl, purinyl, or pyridine-1-oxide-2-yl, the substituent of the substituted group being selected from a halogen, lower alkyl, phenyl, C 2-5 alkenyl, hydroxyl, lower alkoxy, lower alkylthio, nitro, cyano, lower alkylamino, di-lower alkylamino, C 1-10 acylamino, C 1-10 acyl, C 1-10 acyloxy, C 1-10 acyl-lower alkyl, carboxyl, carbamoyl, amino-lower alkyl, N-lower alkylamino-lower alkyl, N,N-di-lower alkyl-amino-lower alkyl, hydroxy-lower alkyl, hydroxyimino-lower alkyl, lower alkoxy-lower alkyl, carboxy-lower alkyl, sulfo-lower alkyl, sulfo, sulfamoyl-lower alkyl, sulfamoyl, carbamoyl-lower alkyl, carbamoyl-C 2-5 alkenyl, and N-hydroxycarbamoyl-lower alkyl; R 3 represents a lower alkyl group; n is 0, 1 or 2; A represents a hydrogen atom or a straight- or branched-chain C 1-14 alkyl group which is unsubstituted or substituted with a halogen, lower alkoxy, cyano, nitro, carboxyl, lower alkoxycarbonyl, hydroxyl, lower alkylthio or C 1-10 acyl group; and B represents a straight- or branched-chain C 1-14 alkyl group which is unsubstituted or substituted with a halogen, hydroxyl, protected hydroxyl, C 1-10 acyl, mercapto, lower alkylthio, nitro, amino, protected amino, imino, protected imino or carboxyl group.
Claim 3
Dependent Claim 41 words
A 7α-methoxycephalosporin or a salt thereof according to claim 1, wherein A represents a hydrogen atom or a lower alkyl group; B represents a C 1-4 alkyl group which is substituted by hydroxyl, protected hydroxyl or halogen; and n is 0.
Claim 4
Dependent Claim 26 words
A 7α-methoxycephalosporin or a salt thereof according to claim 2, wherein R 2 represents an acetoxy group or a substituted or unsubstituted 5-(1,2,3,4-tetrazolyl)thio or 2-(1,3,4-thiadiazolyl)thio group.
Claim 5
Dependent Claim 14 words
A 7α-methoxycephalosporin or a salt thereof according to claim 3, wherein B represents ##STR42##
Claim 6
Dependent Claim 12 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S or R)-hydroxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim 12 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S or R)-hydroxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-hydroxypropionamido]-7.alpha.-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 9
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-hydroxypropionamido]-7.alpha.-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 10
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-propionamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 11
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-propionamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 12
Dependent Claim 9 words
7.beta.-[DL-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(chloromethyl)acetamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 13
Dependent Claim 9 words
7.beta.-[DL-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-α-(chloromethyl)acetamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 14
Dependent Claim 9 words
7β-[D-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[5-(1-β-hydroxyethyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 15
Dependent Claim 9 words
7β-[D-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[5-(1-β-hydroxyethyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 16
Dependent Claim 9 words
7β-[D-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido-β-(S)-hydroxybutanamido]-7α-methoxy-3-acetoxymethyl-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 17
Dependent Claim 9 words
7β-[D-.alpha.-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido-β-(S)-hydroxybutanamido]-7α-methoxy-3-acetoxymethyl-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 18
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[2-(1,3,4-thiadiazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 19
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[2-(1,3,4-thiadiazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 20
Dependent Claim 9 words
7β-[D-α-(4-n-butyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 21
Dependent Claim 9 words
7β-[D-α-(4-n-butyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-hydroxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 22
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-methoxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 23
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-methoxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 24
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-formyloxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 25
Dependent Claim 9 words
7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S)-formyloxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.
Claim 26
Dependent Claim 41 words
A pharmaceutical composition useful for treating bacteria infections in man and mammals which comprises an antibacterially effective amount of a compound or its pharmaceutically acceptable salt as claimed in claim 1, in combination with a pharmaceutically acceptable inert diluent or carrier.
Claim 27
Dependent Claim 27 words
A pharmaceutical composition according to claim 15, wherein the 7α-methoxycephalosporin or its pharmaceutically acceptable salt is 7β-[D-α-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-β-(S or R)-hydroxybutanamido]-7α-methoxy-3-[5-(1-methyl-1,2,3,4-tetrazolyl)thiomethyl]-Δ 3 -cephem-4-carboxylic acid or its pharmaceutically acceptable salt.

References Cited (Backward Citations)

US4087424A Cited
US4045438A Cited
US4129730A Cited
US4103008A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-04-20 1984-10-20 1985-04-21 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-04-20 1988-10-20 1989-04-21 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-04-20 1992-10-20 1993-04-21 $7700.00 Window Closed / Lapsed

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