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US4045438A Expired / Lapsed US ⏱️ 0.0 years remaining

Cephalosporin antibiotics

Assignee: Yeda Research and Development Co Ltd
•
Filing: 1975-10-24
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Granted: 1977-08-30
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Expires: 1995-10-24
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Abstract

Abstract Novel cephalosporin antibiotic derivatives.

Inventors

  • 👤 Fortuna Haviv
  • 👤 Abraham Patchornik

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 10:56
CPC Classifications
C; C07; C07C; C07C247/00; A; A61; A61P; A61P31/00; A61P31/04; C07C57/00; C07C57/52; C07C57/58; C07C57/64; C07C57/76; C07D; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24

Claims Analysis

Total Claims: 34
Claim 1
Independent Claim 309 words
A compound selected from a base of the formula ##STR20## wherein Aryl is selected from phenyl and 2-thienyl; Y is selected from hydrogen, chlorine, bromine, a straight or branched lower alkyl group of from 1 to 4 carbon atoms and a lower alkoxy group of from 1 to 4 carbon atoms with the proviso that when Aryl is 2-thienyl, Y is hydrogen; Z is selected from a bond, oxygen, sulfur and imino with provisio that when Aryl is 2-thienyl, Z is a bond; W is selected from hydrogen, methyl, amino, hydroxy, SO 3 H and COOR 1 wherein R 1 is selected from hydrogen and 5-indanyl; n is zero, 1 or 2 with the proviso that when W is other than hydrogen or methyl and Z is other than a bond, n is not zero; R 2 is selected from hydrogen, and methoxy; M is selected from hydrogen; a pharmaceutically acceptable non-toxic cation; alkanoyloxymethyl wherein the alkanoyl moiety contains from 1 to 5 carbon atoms and may be straight or branched; alkanoylaminomethyl wherein the alkanoyl moitety contains from 1 to 5 carbon atoms and may be straight or branched and wherein the amino nitrogen atom may be substituted with an alkyl group of from 1 to 4 carbon atoms; alkoxycarbonylaminomethyl wherein the alkoxy moitey contains from 1 to 4 carbon atoms and may be straight or branched and wherein the amino nitrogen atom may be substituted with an alkyl group of from 1 to 4 carbon atoms; p-(alkanoyloxy)benzyl wherein the alkanoyl moiety contains from 1 to 5 carbon atoms and may be straight or branched; and aminoalkanoyloxymethyl wherein the alkanoyl moiety contains from 2 to 15 carbon atoms and the amino nitrogen may be mono- or di-substituted with a lower alkyl group of from 1 to 4 carbon atoms; X is hydrogen or acetoxy; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim 309 words
A compound selected from a base of the formula ##STR20## wherein Aryl is selected from phenyl and 2-thienyl; Y is selected from hydrogen, chlorine, bromine, a straight or branched lower alkyl group of from 1 to 4 carbon atoms and a lower alkoxy group of from 1 to 4 carbon atoms with the proviso that when Aryl is 2-thienyl, Y is hydrogen; Z is selected from a bond, oxygen, sulfur and imino with provisio that when Aryl is 2-thienyl, Z is a bond; W is selected from hydrogen, methyl, amino, hydroxy, SO 3 H and COOR 1 wherein R 1 is selected from hydrogen and 5-indanyl; n is zero, 1 or 2 with the proviso that when W is other than hydrogen or methyl and Z is other than a bond, n is not zero; R 2 is selected from hydrogen, and methoxy; M is selected from hydrogen; a pharmaceutically acceptable non-toxic cation; alkanoyloxymethyl wherein the alkanoyl moiety contains from 1 to 5 carbon atoms and may be straight or branched; alkanoylaminomethyl wherein the alkanoyl moitety contains from 1 to 5 carbon atoms and may be straight or branched and wherein the amino nitrogen atom may be substituted with an alkyl group of from 1 to 4 carbon atoms; alkoxycarbonylaminomethyl wherein the alkoxy moitey contains from 1 to 4 carbon atoms and may be straight or branched and wherein the amino nitrogen atom may be substituted with an alkyl group of from 1 to 4 carbon atoms; p-(alkanoyloxy)benzyl wherein the alkanoyl moiety contains from 1 to 5 carbon atoms and may be straight or branched; and aminoalkanoyloxymethyl wherein the alkanoyl moiety contains from 2 to 15 carbon atoms and the amino nitrogen may be mono- or di-substituted with a lower alkyl group of from 1 to 4 carbon atoms; X is hydrogen or acetoxy; and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim 9 words
A compound of claim 1 wherein Aryl is phenyl.
Claim 4
Dependent Claim 12 words
A compound of claim 2 wherein R 2 is in the cis-position.
Claim 5
Dependent Claim 9 words
A compound of claim 1 wherein Aryl is 2-thienyl.
Claim 6
Dependent Claim 12 words
A compound of claim 4 wherein R 2 is in the cis-position.
Claim 7
Dependent Claim 9 words
A compound of claim 1 wherein W is hydrogen.
Claim 8
Dependent Claim 10 words
A compound of claim 6 wherein Z is a bond.
Claim 9
Dependent Claim 11 words
A compound of claim 6 wherein Z is oxygen or sulfur.
Claim 10
Dependent Claim 9 words
A compound of claim 6 wherein Z is imino.
Claim 11
Dependent Claim 9 words
A compound of claim 1 wherein W is methyl.
Claim 12
Dependent Claim 10 words
A compound of claim 10 wherein Z is a bond.
Claim 13
Dependent Claim 11 words
A compound of claim 10 wherein Z is oxygen or sulfur.
Claim 14
Dependent Claim 9 words
A compound of claim 10 wherein Z is imino.
Claim 15
Dependent Claim 9 words
A compound of claim 1 wherein W is hydroxy.
Claim 16
Dependent Claim 10 words
A compound of claim 14 wherein Z is a bond.
Claim 17
Dependent Claim 11 words
A compound of claim 14 wherein Z is oxygen or sulfur.
Claim 18
Dependent Claim 9 words
A compound of claim 14 wherein Z is imino.
Claim 19
Dependent Claim 9 words
A compound of claim 1 wherein W is amino.
Claim 20
Dependent Claim 10 words
A compound of claim 18 wherein Z is a bond.
Claim 21
Dependent Claim 11 words
A compound of claim 18 wherein Z is oxygen or sulfur.
Claim 22
Dependent Claim 9 words
A compound of claim 18 wherein Z is imino.
Claim 23
Dependent Claim 14 words
A compound of claim 1 wherein W is COOR 1 or SO 3 H.
Claim 24
Dependent Claim 10 words
A compound of claim 22 wherein Z is a bond.
Claim 25
Dependent Claim 11 words
A compound of claim 22 wherein Z is oxygen or sulfur.
Claim 26
Dependent Claim 9 words
A compound of claim 22 wherein Z is imino.
Claim 27
Dependent Claim 48 words
A compound selected from a base of the formula: ##STR21## wherein W' is selected from hydrogen, hydroxy, amino, COOH and SO 3 H; X' is hydrogen or acetoxy; and wherein the hydrogen atoms at the 6- and 7-positions are cis to one another; and pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim 48 words
A compound selected from a base of the formula: ##STR21## wherein W' is selected from hydrogen, hydroxy, amino, COOH and SO 3 H; X' is hydrogen or acetoxy; and wherein the hydrogen atoms at the 6- and 7-positions are cis to one another; and pharmaceutically acceptable salts thereof.
Claim 29
Dependent Claim 14 words
A compound of claim 26 which is 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 30
Dependent Claim 14 words
A compound of claim 26 which is 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-hydroxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim 14 words
A compound of claim 26 which is 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 32
Dependent Claim 14 words
A compound of claim 26 which is 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-carboxyacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 33
Dependent Claim 14 words
A compound of claim 26 which is 3-[(acetyloxy)methyl]-7-[[2-[4-(azidomethyl)phenyl]-2-sulfoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and pharmaceutically acceptable salts thereof.
Claim 34
Dependent Claim 14 words
A compound of claim 26 which is 3-methyl-7-[[2-[4-(azidometyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid and pharmaceutically acceptable salts thereof.

References Cited (Backward Citations)

US3341531A Cited
US3865820A Cited
US3812116A Cited
US3920640A Cited
US3919206A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-08-29 1981-02-28 1981-08-30 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-08-29 1985-02-28 1985-08-30 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-08-29 1989-02-28 1989-08-30 $7700.00 Window Closed / Lapsed

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