← Back to Patent Explorer
US4016159A Expired / Lapsed US ⏱️ 0.0 years remaining

Acylamino-cephem-carboxylic acids containing an amidino or guanidino group in the molecule

Assignee: Hoechst AG
•
Filing: 1974-11-27
•
Granted: 1977-04-05
•
Expires: 1994-11-27
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Acylamino-cephem-carboxylic acids of the formula I ##STR1## in which R 1 , R 2 and R 3 represent hydrogen or alkyl, R 1 and R 2 or R 2 and R 3 together may form an alkylene radical which may be substituted, X represents a single bond or NH, A represents a phenylene or thienylene radical which may be substituted, Y represents a single bond or oxygen and Z represents a 5- or 6-membered ring which may be substituted and which may be bound to an anellated ring system, and their physiologically tolerated salts and esters, a process for preparing these compounds and preparations containing them.

Inventors

  • 👤 Dieter Bormann
  • 👤 Bernd Knabe
  • 👤 Elmar Schrinner
  • 👤 Manfred Worm

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 14:34
CPC Classifications
C; C07; C07D; C07D501/00; C07D501/14; C07D501/16; C07D501/20; C07D501/24; C07D501/36; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55

Claims Analysis

Total Claims: 57
Claim 1
Independent Claim 295 words
An acylamino-cephem-carboxylic acid of the formula ##STR464## and physiologically tolerated salts and physiologically tolerated esters thereof, wherein R 1 , R 2 , and R 3 , taken alone, are hydrogen or alkyl having 1 to 8 carbon atoms; R 1 and R 2 , taken together, or R 2 and R 3 , taken together, are alkylene having 2 to 5 carbon atoms, alkylene having 2 to 5 carbon atoms substituted with alkyl having 1 to 4 carbon atoms or with alkyl having 1 to 4 carbon atoms interrupted by an oxygen atom, or are alkylene having 2 to 5 carbon atoms which is ortho- or spiro-fused to 5- or 6-membered cycloalkyl or oxacycloalkyl; X is a single bond or --NH--; A is phenylene, thienylene, or phenylene or thienylene substituted with alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or halogen; Y is a single bond or --O--; and Z is is a heterocyclic ring selected from the group consisting of thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiazolinyl, oxazolyl, oxazolinyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl thiatriazolyl, pyridyl, pyrimidyl, pyrazinyl, pyradiazinyl, thiazinyl, triazinyl, thiadiazinyl, imidazolinyl and tetrahydropyrimidyl, or Z is such a heterocyclic ring substituted by at least one member selected from the group consisting of alkyl having 1 to 15 carbon atoms, cyclopentyl, cyclohexyl, lower alkoxy, lower alkenyl, lower alkylmercapto, lower alkoxycarbonyl, lower alkoxycarbonylamino, amino, lower alkylamino, hydroxy, nitro, phenyl, lower alkoxyphenyl, halophenyl, hydroxyphenyl, aminophenyl, lower alkylphenyl, cetylphenyl, nitrophenyl, biphenylyl, pyridyl, methylpyridyl, furyl, naphthyl, quinolyl, isoquinolyl, thienyl, 2-thiazolyl, 2-pyrrolyl, 4-imidazolyl, 5-pyrazolyl, 4-isoxazolyl, and lower alkyl having 1 to 4 carbon atoms substituted by phenyl, phenoxy, lower alkoxy, or lower alkoxycarbonyl, or Z is such a heterocyclic ring ortho-fused to a benzene ring, or Z is pyridyl-N-oxide or pyridazinyl-N-oxide.
Claim 2
Dependent Claim 295 words
An acylamino-cephem-carboxylic acid of the formula ##STR464## and physiologically tolerated salts and physiologically tolerated esters thereof, wherein R 1 , R 2 , and R 3 , taken alone, are hydrogen or alkyl having 1 to 8 carbon atoms; R 1 and R 2 , taken together, or R 2 and R 3 , taken together, are alkylene having 2 to 5 carbon atoms, alkylene having 2 to 5 carbon atoms substituted with alkyl having 1 to 4 carbon atoms or with alkyl having 1 to 4 carbon atoms interrupted by an oxygen atom, or are alkylene having 2 to 5 carbon atoms which is ortho- or spiro-fused to 5- or 6-membered cycloalkyl or oxacycloalkyl; X is a single bond or --NH--; A is phenylene, thienylene, or phenylene or thienylene substituted with alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, or halogen; Y is a single bond or --O--; and Z is is a heterocyclic ring selected from the group consisting of thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiazolinyl, oxazolyl, oxazolinyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, tetrazolyl thiatriazolyl, pyridyl, pyrimidyl, pyrazinyl, pyradiazinyl, thiazinyl, triazinyl, thiadiazinyl, imidazolinyl and tetrahydropyrimidyl, or Z is such a heterocyclic ring substituted by at least one member selected from the group consisting of alkyl having 1 to 15 carbon atoms, cyclopentyl, cyclohexyl, lower alkoxy, lower alkenyl, lower alkylmercapto, lower alkoxycarbonyl, lower alkoxycarbonylamino, amino, lower alkylamino, hydroxy, nitro, phenyl, lower alkoxyphenyl, halophenyl, hydroxyphenyl, aminophenyl, lower alkylphenyl, cetylphenyl, nitrophenyl, biphenylyl, pyridyl, methylpyridyl, furyl, naphthyl, quinolyl, isoquinolyl, thienyl, 2-thiazolyl, 2-pyrrolyl, 4-imidazolyl, 5-pyrazolyl, 4-isoxazolyl, and lower alkyl having 1 to 4 carbon atoms substituted by phenyl, phenoxy, lower alkoxy, or lower alkoxycarbonyl, or Z is such a heterocyclic ring ortho-fused to a benzene ring, or Z is pyridyl-N-oxide or pyridazinyl-N-oxide.
Claim 3
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1,3,4-Thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-.DELTA.3-cephem-4-carboxylic acid.
Claim 4
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(5-amidino-thienylacetamido)-Δ3-cephem-4-carboxylic acid.
Claim 5
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1,3,4-Thiadiazole-2-yl)-thiomethyl]-7-(5-amidino-thienyl-acetamido)-.DELTA.3-cephem-4-carboxylic acid.
Claim 6
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(Thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ-3-cephem-4-carboxylic acid.
Claim 7
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Methyl-thiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-.DELTA.3-cephem-4-carboxylic acid.
Claim 8
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-guanidino-phenylacetamido)-Δ3-cephem-4-carboxylic acid.
Claim 9
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Methyl-thiazole-2-yl)-thiomethyl]-7-(4-guanidino-phenyl-acetamido)-.DELTA.3-cephem-4-carboxylic acid.
Claim 10
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(Thiazole-2-yl)-thiomethyl]-7-(4-guanidino-phenylacetamido)-Δ3-cephem-4-carboxylic acid.
Claim 11
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-guanidinophenyl-acetamido)-.DELTA.3-cephem-4-carboxylic acid.
Claim 12
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Methyl-thiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 13
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydro-pyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 14
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 15
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Methyl-thiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 16
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,2,4-triazole-3-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 17
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,2,4-triazole-3-yl)-thiomethyl]-7-(4-amidinophenylacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 18
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1,2,4-Triazole-3-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ3-cephem-4-carboxylic acid.
Claim 19
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(1,3,4-Thiadiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido] -Δ3-cephem-4-carboxylic acid.
Claim 20
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidiono-phenylacetamido)-Δ3-cephem-4-carboxylic acid.
Claim 21
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenoxyacetamido] -Δ3-cephem-4-carboxylic acid.
Claim 22
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenoxyacetamido)-Δ3-cephem-4-carboxylic acid hydrochloride.
Claim 23
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-n-Propyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenoxyacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 24
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-oxadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenoxyacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 25
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-n-Propyl-1,3,4-oxadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 26
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenoxyacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 27
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Phenyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 28
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-n-Propyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 29
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-n-Butyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido-Δ3-cephem-4-carboxylic acid.
Claim 30
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Phenyl-1,3,4-oxadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 31
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-n-Propyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 32
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Amino-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 33
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-oxadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ 3-cephem-4-carboxylic acid.
Claim 34
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(1,3,4-Thiadiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenoxyacetamido] -Δ3-cephem-4-carboxylic acid.
Claim 35
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1,3,4-Thiadiazole-2-yl)-thiomethyl]-7-(4-amidonophenoxyacetamido)-.DELTA.3-cephem-4-carboxylic acid.
Claim 36
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(1,3,4-Thiadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenoxyacetamido] -Δ3-cephem-4-carboxylic acid.
Claim 37
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-oxadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenoxyacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 38
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenoxyacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 39
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(5-Methyl-1,3,4-oxadiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenoxyacetamido] -Δ3-cephem-4-carboxylic acid.
Claim 40
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1-Methyl-1H-tetrazole-5-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 41
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(1-Methyl-1H-tetrazole-5-yl)-thiomethyl]-7-[4-amidinophenylacetamido]-.DELTA.3-cephem-4-carboxylic acid.
Claim 42
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(Triazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 43
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-(4-Pyridylthiomethyl)-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 44
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[4,6-Dimethyl-pyrimide-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 45
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4,5-Dimethyl-thiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 46
Dependent Claim 12 words
A compound as claimed in claim 1, which is 3-[(1-Oxido-2-pyridyl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido] -Δ3-cephem-4-carboxylic acid.
Claim 47
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(3-Methyl-1,2,4-thiadiazole-5-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 48
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Isopropyl-thiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 49
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-n-Butyl-thiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 50
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Ethylthiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 51
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(4-Phenylthiazole-2-yl)-thiomethyl]-7-[4-imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 52
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(Benzthiazole-2-yl)-thiomethyl]-7-[4-(imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 53
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[(5-Ethyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 54
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[5-(Ethyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-(1,4,5,6-tetrahydropyrimide-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 55
Dependent Claim 11 words
A compound as claimed in claim 1, which is 3-[5-(Ethyl-1,3,4-thiadiazole-2-yl)-thiomethyl]-7-(4-amidino-phenylacetamido)-Δ3-cephem-4-carboxylic acid.
Claim 56
Dependent Claim 10 words
The compound defined in claim 1, which is 3-[(1-methyl-1-H-tetrazole-5-yl)-thiomethyl]-7-[4-(2-imidazolinyl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.
Claim 57
Dependent Claim 10 words
The compound defined in claim 1, which is 3-[(1,3,4-thiadiazole-2-yl)-thiomethyl]-7-[4-imidazoline-2-yl)-phenylacetamido]-Δ3-cephem-4-carboxylic acid.

References Cited (Backward Citations)

US3855213A Cited
US3865820A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-04-04 1980-10-04 1981-04-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-04-04 1984-10-04 1985-04-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-04-04 1988-10-04 1989-04-05 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag