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US4223031A Expired / Lapsed US ⏱️ 0.0 years remaining

Azolopyrimidinones

Assignee: Mead Johnson and Co LLC
•
Filing: 1978-05-05
•
Granted: 1980-09-16
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Expires: 1998-05-05
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Abstract

Abstract 6-(1H-Tetrazol-5-yl)thiozolo[3,2-a]pyrimidin-5-ones, 3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-ones, and the corresponding imidazo- and triazolo-pyrimidines, thiones, and imines are useful as antiallergy and antiasthmatic compounds by virtue of their inhibitory action on the immediate hypersensitivity reaction in mammals and relaxant action on the tracheal muscle. Intermediates in the synthesis of these substances from 2-aminoazoles and ethoxy-methylene malononitrile also have smooth muscle relaxant and immediate hypersensitivity reaction inhibitory activity.

Inventors

  • 👤 Robert R. Covington
  • 👤 Davis L. Temple, Jr.
  • 👤 Joseph P. Yevich

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 16:44
CPC Classifications
C; C07; C07D; C07D277/00; C07D277/60; A; A61; A61P; A61P11/00; A61P11/08; A61P37/00; A61P37/08; C07D235/00; C07D235/02; C07D235/04; C07D235/24; C07D235/30; C07D249/00; C07D249/02; C07D249/08; C07D249/10; C07D249/14; C07D277/02; C07D277/20; C07D277/32; C07D277/38; C07D277/42; C07D277/62; C07D277/68; C07D277/82; C07D487/00; C07D487/02; C07D487/04; C07D513/00; C07D513/02; C07D513/04

Claims Analysis

Total Claims: 19
Claim 1
Independent Claim 157 words
The 5H-thiazolo[3,2-a]pyrimidine having the following formula and the salts thereof with pharamaceutically acceptable bases ##STR9## wherein R 2 and R 3 are independently selected from H, the substituent A, or taken together with the carbon atoms to which they are attached denote cycloalkenyl having 5 to 7 ring members and up to 2 ring substituents, benzo, monosubstituted benzo, or di-substituted benzo wherein said substituents are independently defined by A, and A is selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkanoyl, alkenoyl, alkylsulfonyl, alkylsulfinyl, alkylthio, alkanoamido, cycloalkyl having 3 to 6 ring members and 1 to 3 optional alkyl substituents, cycloalkylalkyl having 3 to 6 ring members and 1 to 3 optional alkyl substituents, wherein each of the foregoing groups has up to 8 carbon atoms, phenyl, phenylmethyl, trifluoromethyl, nitro, amino, hydroxyl, halogen, carbamoyl, cyano, and cyanoalkyl having from 2 to 4 carbon atoms; Tet is 1H-tetrazol-5-yl; and Z is O, S, or NH.
Claim 2
Dependent Claim 157 words
The 5H-thiazolo[3,2-a]pyrimidine having the following formula and the salts thereof with pharamaceutically acceptable bases ##STR9## wherein R 2 and R 3 are independently selected from H, the substituent A, or taken together with the carbon atoms to which they are attached denote cycloalkenyl having 5 to 7 ring members and up to 2 ring substituents, benzo, monosubstituted benzo, or di-substituted benzo wherein said substituents are independently defined by A, and A is selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkanoyl, alkenoyl, alkylsulfonyl, alkylsulfinyl, alkylthio, alkanoamido, cycloalkyl having 3 to 6 ring members and 1 to 3 optional alkyl substituents, cycloalkylalkyl having 3 to 6 ring members and 1 to 3 optional alkyl substituents, wherein each of the foregoing groups has up to 8 carbon atoms, phenyl, phenylmethyl, trifluoromethyl, nitro, amino, hydroxyl, halogen, carbamoyl, cyano, and cyanoalkyl having from 2 to 4 carbon atoms; Tet is 1H-tetrazol-5-yl; and Z is O, S, or NH.
Claim 3
Dependent Claim 9 words
The compound of claim 1 wherein Z is O.
Claim 4
Dependent Claim 26 words
The compound of claim 1 wherein R 2 and R 3 are independently selected from H and A wherein A is as defined in claim 1.
Claim 5
Dependent Claim 6 words
The compound of claim 3, 3-methyl-6-(1H-tetrazol-5-yl)-5H-thiazolo[3,2-a]pyrimidin-5-one.
Claim 6
Dependent Claim 6 words
The compound of claim 3, 6-(1H-tetrazol-5-yl)-5H-thiazolo[3,2-a]pyrimidin-5-imine.
Claim 7
Dependent Claim 6 words
The compound of claim 3, 6-(1H-tetrazol-5-yl)-5H-thiazolo[3,2-a]pyrimidin-5-one.
Claim 8
Dependent Claim 6 words
The compound of claim 3, 3-phenyl-6-(1H-tetrazol-5-yl)-5H-thiazolo[3,2-a]pyrimidin-5-one.
Claim 9
Dependent Claim 44 words
The 4H-pyrimido[2,1-b]benzothiazole of claim 1 having the following formula and the salts thereof with pharmaceutically acceptable bases ##STR10## wherein R 7 and R 8 are independently selected from H and the substituent A, and A, Tet, and Z are as defined in claim 8.
Claim 10
Dependent Claim 9 words
The compound of claim 8 wherein Z is O.
Claim 11
Dependent Claim 6 words
The compound of claim 8, 3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-one.
Claim 12
Dependent Claim 8 words
The compound of claim 8, 3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-one potassium salt.
Claim 13
Dependent Claim 6 words
The compound of claim 8, 8-methoxy-3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-one.
Claim 14
Dependent Claim 6 words
The compound of claim 8, 7,8-dimethyl-3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-one.
Claim 15
Dependent Claim 6 words
The compound of claim 8, 7,9-dimethyl-3-(1H-tetrazol-5yl)-4H-pyrimido[2,1-b]benzothiazol-4-one.
Claim 16
Dependent Claim 6 words
The compound of claim 8, 8-nitro-3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-one.
Claim 17
Dependent Claim 6 words
The compound of claim 8, 3-(1H-tetrazol-5-yl)-4H-pyrimido[2,1-b]benzothiazol-4-imine.
Claim 18
Dependent Claim 32 words
The method for inhibiting the immediate hypersensitivity reaction in a sensitive mammal which comprises administering to said mammal a non-toxic effective hypersensitivity reaction inhibiting dose of a compound claimed in claim 8.
Claim 19
Dependent Claim 28 words
The method for relieving bronchospasm in a mammal suffering therefrom which comprises administering to said mammal a non-toxic bronchodilator effective dose of a compound claimed in claim 8.

References Cited (Backward Citations)

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US3689488A Cited
US3888983A Cited
US4033961A Cited
US4083980A Cited
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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) 1983-09-16 1984-03-17 1984-09-16 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1987-09-16 1988-03-17 1988-09-16 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1991-09-16 1992-03-17 1992-09-16 $7700.00 Window Closed / Lapsed

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