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US4298734A Expired / Lapsed US ⏱️ 0.0 years remaining

Diazaheterocyclopurines and triazolopyrimidines

Assignee: Mead Johnson and Co LLC
•
Filing: 1979-03-05
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Granted: 1981-11-03
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Expires: 1999-03-05
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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)-one.

Inventors

  • 👤 Davis L. Temple, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-10 02:06
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; C07D487/12; C07D487/14

Claims Analysis

Total Claims: 36
Claim 1
Independent Claim 434 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 6 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 contains 1 or 2 substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups contains 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 12 is lower alkyl, lower alkenyl, lower alkynyl, lower alkylthio, lower alkylsulfinyl, or lower alkylsulfonyl each having up to 8 carbon atoms, hydrogen, thioxo, trifluoromethyl or halogen when R 11 is hydrogen, R 12 is lower alkylamino, di-lower alkylamino, lower alkoxyimino, lower alkyl, lower alkenyl, lower alkynyl, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, or lower alkoxy each having up to 8 carbon atoms, hydrogen, thioxo, trifluoromethyl, halogen, hydrazino, azido, cyano, hydroxy, or amino when R 11 is other than hydrogen, R 14 is selected from the group consisting of lower alkyl having up to 8 carbon atoms, lower alkenyl or lower alkynyl having 3 to 8 atoms, cycloalkyl having 3 to 6 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, lower alkanoyl or lower alkenoyl or lower alkynoyl each having up to 8 carbon atoms, aroyl or substituted aroyl having 7 to 12 carbon atoms, aralkyl or substituted aralkyl having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl having 8 to 12 carbon atoms wherein each of said substituted aroyl, substituted aralkyl, and substituted aryloxyalkyl groups contains 1 or 2 ring substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups contains up to 6 carbon atoms, 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 434 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 6 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 contains 1 or 2 substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups contains 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 12 is lower alkyl, lower alkenyl, lower alkynyl, lower alkylthio, lower alkylsulfinyl, or lower alkylsulfonyl each having up to 8 carbon atoms, hydrogen, thioxo, trifluoromethyl or halogen when R 11 is hydrogen, R 12 is lower alkylamino, di-lower alkylamino, lower alkoxyimino, lower alkyl, lower alkenyl, lower alkynyl, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, or lower alkoxy each having up to 8 carbon atoms, hydrogen, thioxo, trifluoromethyl, halogen, hydrazino, azido, cyano, hydroxy, or amino when R 11 is other than hydrogen, R 14 is selected from the group consisting of lower alkyl having up to 8 carbon atoms, lower alkenyl or lower alkynyl having 3 to 8 atoms, cycloalkyl having 3 to 6 carbon atoms, cycloalkylalkyl having 4 to 12 carbon atoms, pyridylmethyl, lower alkanoyl or lower alkenoyl or lower alkynoyl each having up to 8 carbon atoms, aroyl or substituted aroyl having 7 to 12 carbon atoms, aralkyl or substituted aralkyl having 7 to 12 carbon atoms, aryloxyalkyl or substituted aryloxyalkyl having 8 to 12 carbon atoms wherein each of said substituted aroyl, substituted aralkyl, and substituted aryloxyalkyl groups contains 1 or 2 ring substituents selected from halogen, alkoxy, and alkyl, and each of said alkoxy and alkyl groups contains up to 6 carbon atoms, 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 43 words
The compound of claim 1 having Formula XX wherein R 11 , R 12 , R 6 , R 7 , and R 16 are hydrogen atoms, n is the integer 1, Q is 0, and R 14 is the substituted aralkyl group.
Claim 4
Dependent Claim 6 words
The compound of claim 2, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 5
Dependent Claim 7 words
The compound of claim 2, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-3H-imidazo[1,2-a]purin-9(4H)-one hydrochloride.
Claim 6
Dependent Claim 44 words
The compound of claim 1 having Formula XX wherein R 11 is lower alkyl, R 12 , R 6 , R 7 , and R 16 are hydrogen, n is the integer 1, Q is 0, and R 14 is the substituted aralkyl group.
Claim 7
Dependent Claim 36 words
The compound of claim 1 having formula XX wherein R 11 , R 6 , R 7 , and R 16 are hydrogen, R 12 is alkyl, Q is 0, and R 14 is substituted aralkyl.
Claim 8
Dependent Claim 6 words
The compound of claim 6, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-2-methyl-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 9
Dependent Claim 36 words
The compound of claim 1 having Formula XX wherein R 11 , R 6 , R 7 , and R 16 are hydrogen, R 12 is halogen, Q is 0, and R 14 is substituted aralkyl.
Claim 10
Dependent Claim 42 words
The compound of claim 1 having Formula XX wherein R 11 , R 6 , R 7 , and R 16 are hydrogen, R 12 is lower alkyl, R 14 is lower alkanoyl, n is the integer 1, and Q is 0.
Claim 11
Dependent Claim 41 words
The compound of claim 1 having the Formula XX wherein R 11 , R 12 , R 6 , R 7 , and R 16 are hydrogen, R 14 is lower alkyl, n is the integer 1, and Q is 0.
Claim 12
Dependent Claim 40 words
The compound of claim 1 having the Formula XX wherein R 11 , R 12 , R 6 , R 7 , and R 16 are hydrogen, R 14 is pyridylmethyl, n is the integer 1, and Q is 0.
Claim 13
Dependent Claim 40 words
The compound of claim 1 having the Formula XX wherein R 11 , R 12 , R 6 , R 7 , and R 16 are hydrogen, R 14 is aralkyl, n is the integer 1, and Q is 0.
Claim 14
Dependent Claim 39 words
The compound of claim 1 having Formula XX wherein R 11 , R 12 , R 6 , R 7 , and R 16 are hydrogen, R 14 is arlyoxyalkyl, n is the integer 1 and Q is 0.
Claim 15
Dependent Claim 41 words
The compound of claim 1 having Formula XX wherein R 11 , R 6 , R 7 , and R 16 are hydrogen, R 12 is loweralkylamino, R 14 is substituted aralkyl, n is the integer 1, and Q is 0.
Claim 16
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 6,7-dihydro-2-methyl-4-(2-phenoxyethyl)imidazo[1,2-a]purin-9(4H)-one.
Claim 17
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 6,7-dihydro-2-(1-methylethyl)-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 18
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 6,7-dihydro-2-methyl-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H-one.
Claim 19
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 6,7-dihydro-2-(1-methylethyl)-4-(2-phenoxyethyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 20
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6-methyl-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 21
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-2,6-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 22
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,6-dimethyl-1H-imidazo[1,2-a]purin-9(4H)-one.
Claim 23
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-1,2,6-trimethyl-1H-imidazo[1,2-a]purin9(4H)-one.
Claim 24
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 6,7-dihydro-6-methyl-4-(2-methylpropyl)-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 25
Dependent Claim 23 words
The compound of claim 1 having Formula XX selected from the group consisting of 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,6-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one and a pharmaceutically acceptable acid addition salt thereof.
Claim 26
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,6-dimethyl-3H-imidazo[1,2-a]-purin-9(4H)-one.
Claim 27
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 28
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-trans-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 29
Dependent Claim 9 words
The compound of claim 1 having Formula XX, 4-[(4-chlorophenyl)methyl]-6,7-dihydro-cis-6,7-dimethyl-3H-imidazo[1,2-a]purin-9(4H)-one.
Claim 30
Dependent Claim 29 words
The compound of claim 1 having Formula XX wherein Q is oxo, n is 1, R 16 is hydrogen, and R 6 and R 7 are methyl or ethyl.
Claim 31
Dependent Claim 44 words
A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR27## wherein R 6 , R 7 , R 11 and R 12 are selected from the group consisting of hydrogen and methyl.
Claim 32
Dependent Claim 44 words
A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR27## wherein R 6 , R 7 , R 11 and R 12 are selected from the group consisting of hydrogen and methyl.
Claim 33
Dependent Claim 34 words
A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR28## wherein R 12 is lower alkyl of up to 8 carbon atoms.
Claim 34
Dependent Claim 34 words
A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR28## wherein R 12 is lower alkyl of up to 8 carbon atoms.
Claim 35
Dependent Claim 36 words
A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR29## wherein R 12 is hydrogen or lower alkyl of up to 8 carbon atoms.
Claim 36
Dependent Claim 36 words
A compound selected from the group consisting of those having the following formula and the pharmaceutically acceptable acid addition salts thereof ##STR29## wherein R 12 is hydrogen or lower alkyl of up to 8 carbon atoms.

References Cited (Backward Citations)

US3969506A Cited
US3982000A Cited
US3859289A Cited
US3894022A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-11-02 1985-05-04 1985-11-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-11-02 1989-05-04 1989-11-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-11-02 1993-05-04 1993-11-03 $7700.00 Window Closed / Lapsed

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