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US4404380A Expired / Lapsed US ⏱️ 0.0 years remaining

Triazolopyrimidines

Assignee: Mead Johnson and Co LLC
•
Filing: 1980-08-14
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Granted: 1983-09-13
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Expires: 2000-08-14
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Abstract

Abstract Imidazopyrimidinones and other diazaheterocyclopyrimidinones having an additional fused imidazole or triazole ring have utility as bronchodilators, mediator release inhibitors, phosphodiesterase inhibitors, and peripheral vasodilators. They are orally active and useful in the prophylaxis and treatment of asthma. A preferred compound is 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]-purin-9(4H)-o ne.

Inventors

  • 👤 Davis L. Temple, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-10 01:58
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D487/12; C07D487/14

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 230 words
A compound selected from the group consisting of ##STR26## wherein Q is O, S, or NR 10 , R 10 is selected from the group consisting of hydrogen, lower alkyl having up to 8 carbon atoms, lower alkenyl or lower alkynyl each having 3 to 8 carbon atoms, dialkylaminoalkyl having 4 to 12 carbon atoms, cycloalkyl having 3 to 5 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, aralkyl or substituted aralkyl each having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl each having 8 to 12 carbon atoms wherein each of said substituted aralkyl, and substituted aryloxyalkyl groups having 1 or 2 non-sterically hindering substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups having up to 6 carbon atoms, R 11 is alkoxycarbonyl having 2 to 4 carbon atoms, aminoalkyl having 2 to 8 carbon atoms, or is independently selected from the foregoing group defined for R 10 , R 6 and R 7 are attached to ring carbon atoms and are selected from hydrogen, methyl, and ethyl, R 16 represents hydrogen or a double bond between adjacent ring carbon atoms, n is the integer 1, 2, or 3, the pharmaceutically acceptable acid addition and quaternary ammonium salts of the foregoing compounds, and the pharmaceutically acceptable metal, ammonium, and amine salts of the foregoing compounds wherein R 11 is hydrogen.
Claim 2
Dependent Claim 230 words
A compound selected from the group consisting of ##STR26## wherein Q is O, S, or NR 10 , R 10 is selected from the group consisting of hydrogen, lower alkyl having up to 8 carbon atoms, lower alkenyl or lower alkynyl each having 3 to 8 carbon atoms, dialkylaminoalkyl having 4 to 12 carbon atoms, cycloalkyl having 3 to 5 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, aralkyl or substituted aralkyl each having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl each having 8 to 12 carbon atoms wherein each of said substituted aralkyl, and substituted aryloxyalkyl groups having 1 or 2 non-sterically hindering substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups having up to 6 carbon atoms, R 11 is alkoxycarbonyl having 2 to 4 carbon atoms, aminoalkyl having 2 to 8 carbon atoms, or is independently selected from the foregoing group defined for R 10 , R 6 and R 7 are attached to ring carbon atoms and are selected from hydrogen, methyl, and ethyl, R 16 represents hydrogen or a double bond between adjacent ring carbon atoms, n is the integer 1, 2, or 3, the pharmaceutically acceptable acid addition and quaternary ammonium salts of the foregoing compounds, and the pharmaceutically acceptable metal, ammonium, and amine salts of the foregoing compounds wherein R 11 is hydrogen.
Claim 3
Dependent Claim 37 words
The compound of claim 1 having Formula XI wherein R 11 , R 6 , R 7 , and R 16 are hydrogen, R 14 is substituted aralkyl, n is the integer 1, and Q is 0.
Claim 4
Dependent Claim 6 words
The compound of claim 2, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one.
Claim 5
Dependent Claim 6 words
The compound of claim 2, 4-[2-(3,4-dimethoxyphenyl)ethyl]-6,7-dihydro-3H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one.
Claim 6
Dependent Claim 6 words
The compound of claim 2, 4-[(4-fluorophenyl)methyl]-6,7-dihydro-3H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one.
Claim 7
Dependent Claim 6 words
The compound of claim 2, 4-[(3,4-dichlorophenyl)methyl]-6,7-dihydro-3H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one.
Claim 8
Dependent Claim 7 words
The compound of claim 2, 4-[(3,4-dichlorophenyl)methyl]-6,7-dihydro-3H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one hydrochloride.
Claim 9
Dependent Claim 9 words
The compound of claim 1 having Formula XI, 6,7-dihydro-4-(2-phenoxyethyl)-3H-imidazo[2',1':5,6]-v-triazolo[4,5-a]pyrimidin-9(4H)-one.
Claim 10
Dependent Claim 9 words
The compound of claim 1 having Formula XI, 6,7-dihydro-4-(2-methylpropyl)-3H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one.
Claim 11
Dependent Claim 9 words
The compound of claim 1 having Formula XI, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1-methyl-1H-imidazo[2',1':5,6]-v-triazolo[4,5-d]pyrimidin-9(4H)-one.

References Cited (Backward Citations)

US3859289A Cited
US3949088A Cited
US4327113A Cited
US4007189A Cited
US4053474A Cited
US4296117A Cited
CA1095906A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-09-12 1987-03-14 1987-09-13 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-09-12 1991-03-14 1991-09-13 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-09-12 1995-03-14 1995-09-13 $7700.00 Window Closed / Lapsed

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