US3982011A
Expired / Lapsed
US
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Penicillins
Assignee: Bayer AG
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Filing: 1975-06-11
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Granted: 1976-09-21
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Expires: 1995-06-11
Abstract
Abstract Penicillins of the formula: ##SPC1## And their pharmaceutically acceptable nontoxic salts wherein R 1 is hydrogen, halogen, lower alkyl, hydroxy, nitro or A--NH; A is R 2 , ##EQU1## wherein R 2 is hydrogen, lower alkyl or arylsulphenyl of 6 to 10 carbon atoms; R 3 is hydrogen; lower alkyl; halo-(lower alkyl); cycloalkyl of 3 to 11 carbon atoms, unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicycloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halogen, trifluoromethyl, nitro, amino, alkylsulphonyl of 1 to 4 carbon atoms, and methylenedioxy; azidoaryl of 6 to 10 carbon atoms, azido-(lower alkyl); amino; or thienyl; R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond; CH 2 ; S--CH 2 ; CH=CH; or CO--NH--CH 2 ; E is phenyl or phenyl or thenyl, substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chlorine; and C* is an asymmetric carbon atom, Are useful for their antibacterial activity against both Gram-positive and Gram-negative bacteria.
Inventors
- 👤 Gunter Schmidt
- 👤 Karl Georg Metzger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:23
CPC Classifications
C; C07; C07D; C07D499/00
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
228 words
A pharmaceutical composition for combatting infections in animals and humans comprising an antibacterially effective amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC55## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH-; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl, in combination with a pharmaceutical carrier.
Claim 2
Dependent Claim
228 words
A pharmaceutical composition for combatting infections in animals and humans comprising an antibacterially effective amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC55## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH-; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl, in combination with a pharmaceutical carrier.
Claim 3
Dependent Claim
34 words
A composition according to claim 1 in which in said penicillin R 1 is hydrogen or hydroxy, A is R 3 CO, B is a direct bond and E is phenyl, hydroxyphenyl or thienyl.
Claim 4
Dependent Claim
71 words
A composition according to claim 2 in which in said penicillin R 3 is hydrogen; lower alkyl; chloro(lower)alkyl; dichloro(lower)alkyl; bromo(lower)alkyl; dibromo(lower)alkyl; cycloalkyl of 3 to 7 carbon atoms; cycloalkenyl of 3 to 7 carbon atoms; norbornyl; unsubstituted phenyl; phenyl substituted by 1 to 3 substituents selected from the group consisting of methyl, ethyl, methoxy, ethoxy, chloro, bromo, fluoro, trifluoromethyl, nitro, amino, methylsulfonyl or ethylsulfonyl or substituted by methylenedioxy; amino; or thienyl.
Claim 5
Dependent Claim
25 words
A composition according to claim 3 in which in said penicillin R 1 is hydrogen, R 3 is hydrogen or cycloalkyl and E is phenyl.
Claim 6
Dependent Claim
48 words
A composition according to claim 1 wherein said compound is a salt of said penicillin selected from the group consisting of the sodium, potassium, magnesium, calcium, aluminum, ammonium, a di(lower alkyl)amine, a tri(lower alkyl) amine, procaine, dibenzylamine, N,N'-dibenzylethylenediamine, N-benzyl-β-phenylethylamine, N-methyl-morpholine, N-ethyl-morpholine, 1-ephenamine, dehydroabietylamine, N,N'-bis-dehydroabietylethylenediamine, and N-lower alkylpiperidine salts.
Claim 7
Dependent Claim
28 words
A composition according to claim 1 wherein said penicillin is in the form of the sodium salt and the configuration about the carbon atom designated * is D.
Claim 8
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cyclopropane-carbonylamino-benzoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 9
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cyclopentane-carbonylamino-benzoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 10
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cycloheptane-carbonylamino-benzoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 11
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cyclopentanecarbonylamino-2-hydroxybenzoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 12
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-[4-(4-cycloheptane-1-carbonylamino)benzoyl-amino]-benzylpenicillin or the sodium salt thereof.
Claim 13
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-[4-(4-aminobenzoylamino)benzoylamino]-benzylpenicillin or the sodium salt thereof.
Claim 14
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-[4-(3,4,5-trimethoxybenzoylamino)cinnamoyl-amino]-benzylpenicillin or the sodium salt thereof.
Claim 15
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-[4-(4-methylsulphonylbenzoylamino)benzoylamino]-benzylpenicillin or the sodium salt thereof.
Claim 16
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cyclopentanecarbonylaminobenzoylamino)-p-hydroxybenzylpenicillin or the sodium salt thereof.
Claim 17
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cyclopropanecarbonylamino-cinnamoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 18
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-cyclobutanecarbonylamino-cinnamoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 19
Dependent Claim
17 words
A composition according to claim 1 in which said compound is D-α-(4-formylaminocinnamoylamino)-benzylpenicillin or the sodium salt thereof.
Claim 20
Independent Claim
224 words
The method of combatting infections in animals and humans which comprises administering thereto an antibacterially effective amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC56## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH--; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl.
Claim 21
Independent Claim
224 words
The method of combatting infections in animals and humans which comprises administering thereto an antibacterially effective amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC56## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH--; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl.
Claim 22
Dependent Claim
234 words
A composition for use in promoting growth in animals which comprises at least a growth promoting amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC57## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH--; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl, in combination with a nutritious carrier or animal drinking water.
Claim 23
Dependent Claim
234 words
A composition for use in promoting growth in animals which comprises at least a growth promoting amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC57## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH--; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl, in combination with a nutritious carrier or animal drinking water.
Claim 24
Independent Claim
225 words
The method of enhancing the growth of animals which comprises administering to said animals a growth promoting amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC58## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH--; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl.
Claim 25
Independent Claim
225 words
The method of enhancing the growth of animals which comprises administering to said animals a growth promoting amount of a compound selected from the group consisting of a penicillin of the formula: ##SPC58## and the pharmaceutically acceptable nontoxic salts thereof wherein the carbon atom designated by * is asymmetrically substituted; R 1 is hydrogen, halo, lower alkyl, hydroxy, nitro or A--NH--; A is R 3 CO-- or R 4 CS-- in which R 3 is hydrogen; lower alkyl; halo(lower alkyl); cycloalkyl of 3 to 11 carbon atoms unsubstituted or substituted by hydroxy or alkyl of 1 or 2 carbon atoms; cycloalkenyl of 3 to 11 carbon atoms; bicycloalkyl of up to 8 carbon atoms; bicyloalkenyl of up to 8 carbon atoms; aryl of 6 to 10 carbon atoms, unsubstituted or substituted by from 1 to 3 substituents selected from the group consisting of alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, halo, trifluoromethyl, nitro, amino and alkylsulfonyl of 1 to 4 carbon atoms, or substituted by methylenedioxy, azidoaryl of 6 to 10 carbon atoms; azido(lower alkyl); amino; or thienyl; and R 4 is lower alkylamino or arylamino of 6 to 10 carbon atoms; B is a direct bond or --CH=CH--; and E is phenyl; phenyl substituted by hydroxy, azido, lower alkyl, lower alkoxy, lower alkylthio or chloro; or thienyl.
References Cited (Backward Citations)
US3268513A
Cited
US3433784A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-09-21 | 1980-03-22 | 1980-09-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-09-21 | 1984-03-22 | 1984-09-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-09-21 | 1988-03-22 | 1988-09-21 | $7700.00 | Window Closed / Lapsed |