US4859672A
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Pyrido[2,3-d]pyrimidinone and imidazo[4,5-b]pyrimidinone
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1986-10-29
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Granted: 1989-08-22
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Expires: 2006-10-29
Abstract
Abstract Compounds useful for increasing cardiotonic contractility in humans or other animals and pharmaceutical compositions including these compounds are disclosed. The compounds have the general structure ##STR1## wherein: A is ##STR2## and R 1 , R 2 , R 3 , R 4 , R 8 , R 10 , R 11 , R 12 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 and R 24 are H, lower alkyl of 1-4 carbon atoms, phenyl, substituted phenyl, phenyl lower alkyl of 1-4 carbon atoms or substituted phenyl lower alkyl of 1-4 carbon atoms; wherein the substituted phenyl group is substituted by one or more of lower alkyl, lower alkoxy, amino, lower alkyl amino, lower alkyl mercapto, hydroxy, hydroxy lower alkyl, acetoxy, benzyloxy, phenoxy, lower alkyl sulfinyl or lower alkyl sulfonyl; R 13 is H, lower alkyl of 1-4 carbon atoms, alkoxy lower alkyl of 1-4 carbon atoms, hydroxy lower alkyl of 1-5 carbon atoms, amino, carbamoyl, cyano, lower alkyl carbamoyl of 1-4 carbon atoms, formyl, amino lower alkyl of 1-4 carbon atoms, carboxy, carbalkoxy, or tetrazolyl; R 3 and R 4 together may form =O; R 16 and R 17 together may form a carbon-carbon bond; n is 0 or 1; and O is 0 or 1.
Inventors
- 👤 Alfred P. Spada
- 👤 Henry F. Campbell
- 👤 Donald E. Kuhla
- 👤 William L. Studt
- 👤 William C. Faith
- 👤 Bruce F. Molino
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 23:44
CPC Classifications
C; C07; C07D; C07D475/00; A; A61; A61P; A61P37/00; A61P37/02; A61P37/04; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
203 words
A compound having the structure: ##STR7## or a pharmaceutically acceptable salt thereof wherein: A is ##STR8## and R 1 , R 2 , R 3 , R 4 , R 8 , R 10 , R 11 , R 12 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 and R 24 are H, lower alkyl of 1-4 carbon atoms or substituted phenyl lower alkyl of 1-4 carbon atoms; wherein the substituted phenyl group is substituted by one or more of lower alkyl, lower alkoxy, amino, lower alkyl amino, lower alkyl mercapto, hydroxy, hydroxy lower alkyl, acetoxy, benzyloxy, phenoxy, lower alkyl sulfinyl or lower alkyl sulfonyl; R 13 is H, lower alkyl of 1-4 carbon atoms, alkoxy lower alkyl of 1-4 carbon atoms, hydroxy lower alkyl of 1-5 carbon atoms, amino, carbamoyl, cyano, lower allkyl carbamoyl of 1-4 carbon atoms, formyl, amino lower alkyl of 1-4 carbon atoms, carboxy, carbalkoxy, or tetrazolyl; R 3 and R 4 together may form=0; R 16 and R 17 together may form a carbon-carbon bond; n is 0 or 1; and Q is 0 or 1.
Claim 2
Dependent Claim
203 words
A compound having the structure: ##STR7## or a pharmaceutically acceptable salt thereof wherein: A is ##STR8## and R 1 , R 2 , R 3 , R 4 , R 8 , R 10 , R 11 , R 12 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 20 , R 21 , R 22 , R 23 and R 24 are H, lower alkyl of 1-4 carbon atoms or substituted phenyl lower alkyl of 1-4 carbon atoms; wherein the substituted phenyl group is substituted by one or more of lower alkyl, lower alkoxy, amino, lower alkyl amino, lower alkyl mercapto, hydroxy, hydroxy lower alkyl, acetoxy, benzyloxy, phenoxy, lower alkyl sulfinyl or lower alkyl sulfonyl; R 13 is H, lower alkyl of 1-4 carbon atoms, alkoxy lower alkyl of 1-4 carbon atoms, hydroxy lower alkyl of 1-5 carbon atoms, amino, carbamoyl, cyano, lower allkyl carbamoyl of 1-4 carbon atoms, formyl, amino lower alkyl of 1-4 carbon atoms, carboxy, carbalkoxy, or tetrazolyl; R 3 and R 4 together may form=0; R 16 and R 17 together may form a carbon-carbon bond; n is 0 or 1; and Q is 0 or 1.
Claim 3
Dependent Claim
30 words
A method for increasing cardiac contractility in a human or other animal requiring such treatment which comprises administering thereto an effective inotropic amount of a compound according to claim 1.
Claim 4
Dependent Claim
35 words
A pharmaceutical composition for increasing cardiac contractility in a human or other animal requiring such treatment comprising an effective inotropic amount of a compound according to claim 1 in admixture with a pharmaceutically acceptable carrier.
Claim 5
Dependent Claim
24 words
A compound of claim 1 wherein R 8 and R 10 are hydrogen; R 3 and R 4 are each hydrogen or together form=0.
Claim 6
Dependent Claim
9 words
A compound of claim 4 wherein A is: ##STR9##
Claim 7
Dependent Claim
9 words
A compound of claim 4 wherein A is ##STR10##
Claim 8
Dependent Claim
9 words
A compound of claim 4 wherein A is: ##STR11##
Claim 9
Dependent Claim
142 words
A compound according to the structure: ##STR12## or a pharmaceutically acceptable salt thereof, wherein n is 0 or 1; R 1 is H or lower alkyl of 1-4 carbon atoms; R 2 is H or lower alkyl of 1-4 carbon atoms; R 3 is H or lower alkyl of 1-4 carbon atoms; R 4 is H or lower alkyl of 1-4 carbon atoms; R 8 is H or lower alkyl of 1-4 carbon atoms; R 10 is H or lower alkyl of 1-4 carbon atoms; R 15 is H or lower alkyl of 1-4 carbon atoms; R 16 is H or lower alkyl of 1-4 carbon atoms; R 17 is H or lower alkyl of 1-4 carbon atoms; R 16 and R 17 may together form a carbon-carbon double bond; and R 18 is H or lower alkyl of 1-4 carbon atoms.
Claim 10
Dependent Claim
142 words
A compound according to the structure: ##STR12## or a pharmaceutically acceptable salt thereof, wherein n is 0 or 1; R 1 is H or lower alkyl of 1-4 carbon atoms; R 2 is H or lower alkyl of 1-4 carbon atoms; R 3 is H or lower alkyl of 1-4 carbon atoms; R 4 is H or lower alkyl of 1-4 carbon atoms; R 8 is H or lower alkyl of 1-4 carbon atoms; R 10 is H or lower alkyl of 1-4 carbon atoms; R 15 is H or lower alkyl of 1-4 carbon atoms; R 16 is H or lower alkyl of 1-4 carbon atoms; R 17 is H or lower alkyl of 1-4 carbon atoms; R 16 and R 17 may together form a carbon-carbon double bond; and R 18 is H or lower alkyl of 1-4 carbon atoms.
Claim 11
Dependent Claim
54 words
A compound according to the structure: ##STR13## or a pharmaceutically acceptable salt thereof, wherein R 1 is H or methyl; R 2 is H or methyl; R 3 is H; R 4 is H, methyl, or together with R 3 forms=0; R 8 is H, or methyl; and R 10 is H, or methyl.
Claim 12
Dependent Claim
54 words
A compound according to the structure: ##STR13## or a pharmaceutically acceptable salt thereof, wherein R 1 is H or methyl; R 2 is H or methyl; R 3 is H; R 4 is H, methyl, or together with R 3 forms=0; R 8 is H, or methyl; and R 10 is H, or methyl.
Claim 13
Dependent Claim
7 words
A compound of claim 9 being 6-[6'-(4',5'-Dihydro-3(2H)-3-pyridazinyl)]-3,4-dihydro-1-methyl-pyrido-[2,3-d]pyrimidin-2-(1H)-one.
Claim 14
Dependent Claim
7 words
A compound of claim 5 being 6-[3'-Cyano-6'-methyl-2'-oxo-(1H)pyridin-5'-yl]-3,4-dihydro-1,3-dimethylpyrido[2,3-d]pyrimidin-2(1H)-one.
Claim 15
Dependent Claim
7 words
A compound of claim 6 being 6-[6'-Methyl-2'-oxo-(1H)pyrimidin-4'-yl]-3,4-dihydro-1-methylpyrido[2,3-d]pyrimidin-2(1H)-one.
Claim 16
Dependent Claim
8 words
A compound of claim 7 being 6- [2',6'-Dioxo-(1H,5H)pyrimidin-4'-yl]-3,4-dihydro-1-methylpyrido[2,3-d]pyrimidin-2(1H)-one.
Claim 17
Dependent Claim
7 words
A compound of claim 1 being 6-[3'-cyano-6'-methyl-2'-oxo-(1H)pyridin-5'-yl]-3,4-dihydro-1,3-dimethylpyrido[3,4-d]pyrimidin-2(1H)-one.
Claim 18
Dependent Claim
7 words
A compound of claim 9 being 6[6'-(4',5'-Dihydro-3(2H)-3-oxo-pyridazinyl)]1,3-dimethylpyrido[2,3-d]pyrimidin-2,4-(1H,3H)-dione.
Claim 19
Dependent Claim
7 words
A compound of claim 1 being 6-[3'-Cyano-6'-methyl-2'-oxo-(1H)pyridin-5'-yl]-1,3-dimethyl-2H-imidazo[4,5-b]pyrindin-2-one.
Claim 20
Dependent Claim
7 words
A compound of claim 5 being 6-[3'-Cyano-6'-methyl-2'-oxo-(1H)pyridin-5'-yl]-1,3-dimethylpyridio[2,3-d]pyrimidin-2,4-(1H,3H)-dione.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-08-21 | 1993-02-20 | 1993-08-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-08-21 | 1997-02-20 | 1997-08-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-08-21 | 2001-02-20 | 2001-08-22 | $7700.00 | Window Closed / Lapsed |