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US3878212A Expired / Lapsed US ⏱️ 0.0 years remaining

Blood sugar lowering sulfamoyl pyrimidines and asymmetrical carbon atom

Assignee: Individual
•
Filing: 1973-07-05
•
Granted: 1975-04-15
•
Expires: 1993-07-05
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Abstract

Abstract which have available an asymmetrical C atom C*, the enantiomers exhibit a surprisingly great difference in the blood sugar lowering effect. Thus, one of the enantiomers is generally 30 to 300 times more effective than the other and about twice as effective as the racemate. Compounds of the sulfamoyl pyrimidine with asymetric carbon atom are provided for the treatment of Diabetes Mellitus. Substituted sulfonamides are suitable for the treatment of Diabetes mellitus. The first clinically tested preparation of this class of substances, N-sulfanilyl-N''-n-butyl urea (Carbutamid), still showed undesirable bacteriostatic side effects. These side effects no longer appear, for example, in N-(4methylbenzenesulfonyl)-N''-n-butyl urea (Tolbutamid) or in N-(5(2-methoxyethoxy)-2-pyrimidinyl)-sulfamoyl-benzene (Glymidin). The clinically employed dose of the last-named compounds is of the order of 0.5 - 1 g daily. The p-substitution of the benzene nucleus in the Glymidin type, in particular the subsitution by aromatic acid amide groups, leads to compounds of considerably increased action, as is evident from Belgian Pat. No. 726,253. It has now been found that in compounds of the general formula I

Inventors

  • 👤 Clemens Rufer
  • 👤 Hans Ahrens
  • 👤 Helmut Biere
  • 👤 Eberhard Schroder
  • 👤 Erich Gerhards
  • 👤 Ekkehard Schillinger
  • 👤 Wolfgang Felix Losert
  • 👤 Olaf Loge

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 19:28
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/69

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 11 words
RACEMATES AND OPTICAL ANTIPODES OF SULFAMOYL PYRIMIDINES OF THE GENERAL FORMULA
Claim 2
Dependent Claim 11 words
RACEMATES AND OPTICAL ANTIPODES OF SULFAMOYL PYRIMIDINES OF THE GENERAL FORMULA
Claim 3
Dependent Claim 12 words
A compound as set forth in claim 1, which is S(-)-4-(N-(5-isopropoxy-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-propylamide.
Claim 4
Dependent Claim 12 words
A compound as set forth in claim 1, which is R(+)-4-(N-(5-isopropoxy-2-pyrimidinyl)-sulfamoyl)-phenylacetic-1-phenyl -propylamide.
Claim 5
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isopropoxy-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-propylamide.
Claim 6
Dependent Claim 12 words
A compound as set forth in claim 1, which is S(-)-4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-propylamide.
Claim 7
Dependent Claim 12 words
A compound as set forth in claim 1, which is R(+)-4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-propylamide.
Claim 8
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-propylamide.
Claim 9
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isopropoxy-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-butylamide.
Claim 10
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isopropoxy-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-phenyl-2-methyl-propylamide.
Claim 11
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isopropoxy-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-2-phenyl-2-butylamide.
Claim 12
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-(5-fluoro-2-methoxy-phenyl)-ethylamide.
Claim 13
Dependent Claim 12 words
A compound as set forth in claim 1, which is S-(-4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-(5-fluoro-2-methoxy-phenyl)-ethylamide.
Claim 14
Dependent Claim 12 words
A compound as set forth in claim 1, which is R-(+)-4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-(5-fluor-2-methoxy-phenyl)-ethylamide.
Claim 15
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5(-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-methoxy-carbonyl-benzylamide.
Claim 16
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylaceTic acid-1-carboxy-benzylamide.
Claim 17
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-1-methyl-2-phenyl-ethylamide.
Claim 18
Dependent Claim 12 words
A compound as set forth in claim 1, which is 4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-phenylpropylamide.
Claim 19
Dependent Claim 12 words
A compound as set forth in claim 1, which is R-(+)-4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenlacetic acid-2-phenylpropylamide.
Claim 20
Dependent Claim 12 words
A compound as set forth in claim 1, which is S-(-)-4-(N-(5-isobutyl-2-pyrimidinyl)-sulfamoyl)-phenylacetic acid-2-phenylpropylamide.

References Cited (Backward Citations)

US3621026A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-04-14 1978-10-14 1979-04-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-04-14 1982-10-14 1983-04-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-04-14 1986-10-14 1987-04-15 $7700.00 Window Closed / Lapsed

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