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US3326759A Expired / Lapsed US ⏱️ 0.0 years remaining

Antibiotics macrocin and lactenocin

Assignee: Eli Lilly and Co
•
Filing: 1962-07-19
•
Granted: 1967-06-20
•
Expires: 1982-07-19
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Abstract

No abstract record available.

Inventors

  • 👤 Robert L Hamill
  • 👤 William M Stark

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 10:28
CPC Classifications
C; C07; C07H; C07H17/00; C07H17/04; C07H17/08; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/886; Y10S435/896

Claims Analysis

Total Claims: 4
Claim 1
Independent Claim 382 words
A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE ANTIBIOTIC MACROCIN AND ITS ACID ADDITION SALTS, SAID ANTIBIOTIC BEING A WHITE SOLID MELTING AT ABOUT 134-136*C. CRYSTALLIZING IN THE FORM OF SMALL TRANSPARENT COLORLESS BLADES; HAVING A PK''Z=7.0 WHEN DETERMINED IN A 2:1 DIMETHYLFORMAMIDE-WATER SOLUTION; HAVING MOLECULAR WEIGHT OF ABOUT 909; GIVING THE FOLLOWING AVERAGE VALUES UPON ELEMENTAL ANALYSIS AFTER DRYING IN VACUO AT ABOUT 80*C.: CARBON, 60.99 PERCENT; HYDROGEN, 8.50 PERCENT; NITROGEN, 1.45 PERCENT; OXYGEN (BY DIFFERENCE), 29.06 PERCENT; HAVING AN EMPIRICAL FORMULA CORRESPONDING TO C46H79NO17; ANALYZING FOR ONE METHOXY GROUP, TWO N-METHYL GROUPS AND AT LEAST SIX C-METHYL GROUPS; HAVING AN INFRARED ABSORPTION SPECTRUM IN CHLOROFORM SOLUTION SUBSTANTIALLY AS SHOWN IN FIGURE 1 IN THE ACCOMPANYING DRAWINGS AND HAVING THE FOLLOWING ABSORPTION BANDS GIVEN IN MICRONS:2.81, 3.35, 3.40, 5.81, 5.95, 6.28, 6.88, 7.10, 7.27, 7.62, 7.89, 8.45, 8.61, 8.78, 8.98, 9.30, 9.53, 9,88, 10.05, 10.15, 10.45, 10.81, 11.10, 11.55, AND 11.90; HAVING A NUCLEAR MAGNETIC RESONANCE ABSORPTION SPECTRUM SUBSTANTIALLY AS SHOWN IN FIGURE 3 OF THE ACCOMPANYING DRAWINGS; HAVING AN ULTRAVIOLET SPECTRUM IN AQUEOUS SOLUTION CHARACTERIZED BY AN ABSORPTION MAXIMUM AT ABOUT 282 MU WITH A MOLAR EXTINCTION: HAVING A SPECIFIC ROTATION (A)D25=-52.50 (C=2 PERCENT IN METHANOL (W./V.)); ITRS CRYSTALS SHOWING THE FOLLOWING INTERPLANAR DISTANCES WHEN BEING SUBJECTED TO UNFILTERED CHROMIUM X-RADIATION AT A WAVE-LENGTH OF 2.2896 A.; 11.70, 10.21, 9.20, 7.55, 6.88, 6.36, 6.04, 5.63, 5.36, 5.09, 4,96, 4,59, 4.37, 4.09, 3.94, 3.79, 3.65, 3.51, 3.39, 3.19, 3.00, 2.92, 2.76, 2.69, 2.59, 2.49, 2.33, 2.27, 2.20, 2.15, 2.10, 2.06, 2.01, 1.963, AND 1.904; GIVING POSITIVE MOLISCH AND ANTHRONE TESTS AND NEGATIVE NINHYDRIN, BIURET AND SAKAGUCHI PROTEIN TESTS; DECOLORIZING PERMANGANATE SOLUTION; GIVING THE FOLLOWING R1 VALUES ON PAPER CHROMATOGRAPHY; 0.43 IN A METHYL ETHYL KETONE SOLVENT ON PH 4 BUFFERED PAPER; 0.66 IN METHYL ETHYL KETONE; 0.92 IN AN N-BUTANOL SATURATRED WITH WATER SOLVENT SYSTEM ON PH 4 BUFFERED PAPER; AND 0.74 IN WATER CONTAINING 7 PERCENT OF SODIUM CHLORIDE AND 2.5 PERCENT METHYL ETHYL KETONE; GIVING UPON TREATMENT WITH AQUEOUS ACID AT A PH IN THE RANGE OF ABOUT TWO TO THREE, THE CARBOHYDRATE, MYCAROSE AND THE ANTIBIOTIC, LACTENOCIN; AND STRONGLY INHIBITING THE FOLLOWING MICRO-ORGANISMS: STAPHYLOCOCCUS AUREUS, STAPHYLOCOCCUS ALBUS, B. SUBTILIS, SACRINA LUTEA, M. TUBERCULOSIS (607), M. AVIUM, DIPLOCOCCUS PNEUMONIAE (PARK I), STREPTOCOCCUS C203, C. DIPHTHERIAE, AND C. MICHIGANENSE.
Claim 2
Dependent Claim 382 words
A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE ANTIBIOTIC MACROCIN AND ITS ACID ADDITION SALTS, SAID ANTIBIOTIC BEING A WHITE SOLID MELTING AT ABOUT 134-136*C. CRYSTALLIZING IN THE FORM OF SMALL TRANSPARENT COLORLESS BLADES; HAVING A PK''Z=7.0 WHEN DETERMINED IN A 2:1 DIMETHYLFORMAMIDE-WATER SOLUTION; HAVING MOLECULAR WEIGHT OF ABOUT 909; GIVING THE FOLLOWING AVERAGE VALUES UPON ELEMENTAL ANALYSIS AFTER DRYING IN VACUO AT ABOUT 80*C.: CARBON, 60.99 PERCENT; HYDROGEN, 8.50 PERCENT; NITROGEN, 1.45 PERCENT; OXYGEN (BY DIFFERENCE), 29.06 PERCENT; HAVING AN EMPIRICAL FORMULA CORRESPONDING TO C46H79NO17; ANALYZING FOR ONE METHOXY GROUP, TWO N-METHYL GROUPS AND AT LEAST SIX C-METHYL GROUPS; HAVING AN INFRARED ABSORPTION SPECTRUM IN CHLOROFORM SOLUTION SUBSTANTIALLY AS SHOWN IN FIGURE 1 IN THE ACCOMPANYING DRAWINGS AND HAVING THE FOLLOWING ABSORPTION BANDS GIVEN IN MICRONS:2.81, 3.35, 3.40, 5.81, 5.95, 6.28, 6.88, 7.10, 7.27, 7.62, 7.89, 8.45, 8.61, 8.78, 8.98, 9.30, 9.53, 9,88, 10.05, 10.15, 10.45, 10.81, 11.10, 11.55, AND 11.90; HAVING A NUCLEAR MAGNETIC RESONANCE ABSORPTION SPECTRUM SUBSTANTIALLY AS SHOWN IN FIGURE 3 OF THE ACCOMPANYING DRAWINGS; HAVING AN ULTRAVIOLET SPECTRUM IN AQUEOUS SOLUTION CHARACTERIZED BY AN ABSORPTION MAXIMUM AT ABOUT 282 MU WITH A MOLAR EXTINCTION: HAVING A SPECIFIC ROTATION (A)D25=-52.50 (C=2 PERCENT IN METHANOL (W./V.)); ITRS CRYSTALS SHOWING THE FOLLOWING INTERPLANAR DISTANCES WHEN BEING SUBJECTED TO UNFILTERED CHROMIUM X-RADIATION AT A WAVE-LENGTH OF 2.2896 A.; 11.70, 10.21, 9.20, 7.55, 6.88, 6.36, 6.04, 5.63, 5.36, 5.09, 4,96, 4,59, 4.37, 4.09, 3.94, 3.79, 3.65, 3.51, 3.39, 3.19, 3.00, 2.92, 2.76, 2.69, 2.59, 2.49, 2.33, 2.27, 2.20, 2.15, 2.10, 2.06, 2.01, 1.963, AND 1.904; GIVING POSITIVE MOLISCH AND ANTHRONE TESTS AND NEGATIVE NINHYDRIN, BIURET AND SAKAGUCHI PROTEIN TESTS; DECOLORIZING PERMANGANATE SOLUTION; GIVING THE FOLLOWING R1 VALUES ON PAPER CHROMATOGRAPHY; 0.43 IN A METHYL ETHYL KETONE SOLVENT ON PH 4 BUFFERED PAPER; 0.66 IN METHYL ETHYL KETONE; 0.92 IN AN N-BUTANOL SATURATRED WITH WATER SOLVENT SYSTEM ON PH 4 BUFFERED PAPER; AND 0.74 IN WATER CONTAINING 7 PERCENT OF SODIUM CHLORIDE AND 2.5 PERCENT METHYL ETHYL KETONE; GIVING UPON TREATMENT WITH AQUEOUS ACID AT A PH IN THE RANGE OF ABOUT TWO TO THREE, THE CARBOHYDRATE, MYCAROSE AND THE ANTIBIOTIC, LACTENOCIN; AND STRONGLY INHIBITING THE FOLLOWING MICRO-ORGANISMS: STAPHYLOCOCCUS AUREUS, STAPHYLOCOCCUS ALBUS, B. SUBTILIS, SACRINA LUTEA, M. TUBERCULOSIS (607), M. AVIUM, DIPLOCOCCUS PNEUMONIAE (PARK I), STREPTOCOCCUS C203, C. DIPHTHERIAE, AND C. MICHIGANENSE.
Claim 3
Dependent Claim 262 words
A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE ANTIOBIOTIC LACTENOCIN, AND ITS ACID ADDITION SALTS, SAID ANTBIOTIC LACTENOCIN HAVING A PK''A=7.8 WHEN TITRATED IN 2:1 DIMETHYLFORMAMIDE-WATER; HAVING A MOLECULAR WEIGHT OF ABOUT 770; HAVING AN AVERAGE ELEMENTAL ANALYSIS AFTER DRYING IN VACUO AT 80*C. AS FOLLOWS: CARBON, 59.77 PERCENT; HYDROGEN, 8.62 PERCENT; NITROGEN, 1.78 PERCENT; OXYGEN (BY DIFFERENCE) 29.83 PERCENT; HAVING AN EMPIRICAL FORMULA CORRESPONDING TO C39H63NO14; HAVING AN INFRARED ABSORPTION SPECTRUM IN CHLOROFORM SOLUTION SUBSTANTIALLY AS SHOWN IN FIGURE 2 OF THE ACCOMPANYING DRAWINGS AND HAVING THE FOLLOWING ABSORPTION BANDS GIVEN IN MICRONS: 2.80, 3.35, 3.40, 5.81, 5.95, 6.28, 6.88, 7.11, 7.25, 7.61, 7.89, 8.45, 8.77, 9.27, 9.45, 9.92, 10.12, 10.42, 10.81, 11.10, 11.55, AND 11.97; HAVING A NUCLEAR MAGNETIC RESONANCE ABSORPTION SPECTRUM SUBSTANTIALLY AS SHOWN IN FIGURE 4 OF THE ACCOMPANYING DRAWINGS; HAVING AN ULTRAVIOLET SPECTRUM IN AQUEOUS SOLUTION CHARACTERIZED BY AN ABSORPTION MAXIMUM AT 283 MU WITH A MOLAR EXTINCTION: GIVING POSITIVE TESTS FOR METHOXY, HYDROXY, N-METHYL AND C-METHYL GROUPS ON GROUP DETERMINATION; GIVING A POSITIVE MOLISCH TEST, NEGATIVE NINHYDRIN, BIURET, SAKAGUCHI PROTEIN, AND FERRIC CHLORIDES TESTS; DECOLORIZING PERMANGANATE SOLUTION; GIVING THE FOLLOWING RF VALUES ON PAPER CHROMATOGRAPHY: 0.20 N A METHYL ETHYL KETONE SOLVENT SYSTEM USING PH 4 BUFFERED PAPER; 0.38 IN A METHYL ETHYL KETONE SOLVENT SYSTEM; 0.60 IN AN N-BUTANOL SATURATED WITH WATER SOLVENT SYSTEM; AND 0.86 IN AN AQUEOUS SOLVENT SYSTEM CONTAINING 7 PERCENT SODIUM CHLORIDE AND 2.5 PERCENT METHYL ETHYL KETONE; AND SHOWING PRONOUNCED INHIBITORY ACTIVITY AGAINST THE FOLLOWING MICROORGANISMS: STAPHYLOCOCCUS AUREUS, STAPHYLOCOCCUS ALBUS, B. SUBTILIS, SARCINA LUTEA, M. AVIUM, AND C. MICHIGANESE.
Claim 4
Dependent Claim 262 words
A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE ANTIOBIOTIC LACTENOCIN, AND ITS ACID ADDITION SALTS, SAID ANTBIOTIC LACTENOCIN HAVING A PK''A=7.8 WHEN TITRATED IN 2:1 DIMETHYLFORMAMIDE-WATER; HAVING A MOLECULAR WEIGHT OF ABOUT 770; HAVING AN AVERAGE ELEMENTAL ANALYSIS AFTER DRYING IN VACUO AT 80*C. AS FOLLOWS: CARBON, 59.77 PERCENT; HYDROGEN, 8.62 PERCENT; NITROGEN, 1.78 PERCENT; OXYGEN (BY DIFFERENCE) 29.83 PERCENT; HAVING AN EMPIRICAL FORMULA CORRESPONDING TO C39H63NO14; HAVING AN INFRARED ABSORPTION SPECTRUM IN CHLOROFORM SOLUTION SUBSTANTIALLY AS SHOWN IN FIGURE 2 OF THE ACCOMPANYING DRAWINGS AND HAVING THE FOLLOWING ABSORPTION BANDS GIVEN IN MICRONS: 2.80, 3.35, 3.40, 5.81, 5.95, 6.28, 6.88, 7.11, 7.25, 7.61, 7.89, 8.45, 8.77, 9.27, 9.45, 9.92, 10.12, 10.42, 10.81, 11.10, 11.55, AND 11.97; HAVING A NUCLEAR MAGNETIC RESONANCE ABSORPTION SPECTRUM SUBSTANTIALLY AS SHOWN IN FIGURE 4 OF THE ACCOMPANYING DRAWINGS; HAVING AN ULTRAVIOLET SPECTRUM IN AQUEOUS SOLUTION CHARACTERIZED BY AN ABSORPTION MAXIMUM AT 283 MU WITH A MOLAR EXTINCTION: GIVING POSITIVE TESTS FOR METHOXY, HYDROXY, N-METHYL AND C-METHYL GROUPS ON GROUP DETERMINATION; GIVING A POSITIVE MOLISCH TEST, NEGATIVE NINHYDRIN, BIURET, SAKAGUCHI PROTEIN, AND FERRIC CHLORIDES TESTS; DECOLORIZING PERMANGANATE SOLUTION; GIVING THE FOLLOWING RF VALUES ON PAPER CHROMATOGRAPHY: 0.20 N A METHYL ETHYL KETONE SOLVENT SYSTEM USING PH 4 BUFFERED PAPER; 0.38 IN A METHYL ETHYL KETONE SOLVENT SYSTEM; 0.60 IN AN N-BUTANOL SATURATED WITH WATER SOLVENT SYSTEM; AND 0.86 IN AN AQUEOUS SOLVENT SYSTEM CONTAINING 7 PERCENT SODIUM CHLORIDE AND 2.5 PERCENT METHYL ETHYL KETONE; AND SHOWING PRONOUNCED INHIBITORY ACTIVITY AGAINST THE FOLLOWING MICROORGANISMS: STAPHYLOCOCCUS AUREUS, STAPHYLOCOCCUS ALBUS, B. SUBTILIS, SARCINA LUTEA, M. AVIUM, AND C. MICHIGANESE.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1970-06-19 1970-12-19 1971-06-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1974-06-19 1974-12-19 1975-06-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1978-06-19 1978-12-19 1979-06-20 $7700.00 Window Closed / Lapsed

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