US5137890A
Expired / Lapsed
US
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4-phenyl tetrahydropyrido(4,3-d)pyrimidines
Assignee: Ortho Pharmaceutical Corp
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Filing: 1990-02-14
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Granted: 1992-08-11
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Expires: 2010-02-14
Abstract
Abstract ##STR1## Novel tetrahydropyrido[4,3-d]pyrimidines and their synthesis are described. These compounds are useful for the treatment of gastrointestinal diseases, and are particularly useful as cytoprotective agents to prevent ulcer formation.
Inventors
- 👤 Pauline J. Sanfilippo
- 👤 Jeffery B. Press
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 04:36
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
284 words
A compound of the formula ##STR9## where R 1 is C 1 -C 3 alkyl, thiol, alkylthio, amino or substituted amino, wherein said substituted amino is substituted either singularly or in combination with C 1 -C 3 alkyl, C 2 -C 4 acyl, phenyl or substituted phenyl, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 2 -C 4 acyl or trifluoromethyl; R 2 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, amino or substituted amino, wherein said substituted amino is substituted either singularly or in combination with C 1 -C 3 alkyl, C 2 -C 4 acyl, phenyl or substituted phenyl, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl; and R 3 is hydrogen, C 2 -C 4 acyl, benzoyl, substituted benzoyl, C 1 -C 4 alkyl, substituted C 1 -C 4 alkyl or allyl, wherein said substituted benzoyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl, and said substituted alkyl is substituted either singularly or in combination with halogen, phenyl, substituted phenyl, amino or substituted amino, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl, and said substituted amino is substituted either singularly or in combination with C 1 -C 3 alkyl, C 1 -C 5 cycloalkyl, phenyl or substituted phenyl, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl and their salts.
Claim 2
Dependent Claim
284 words
A compound of the formula ##STR9## where R 1 is C 1 -C 3 alkyl, thiol, alkylthio, amino or substituted amino, wherein said substituted amino is substituted either singularly or in combination with C 1 -C 3 alkyl, C 2 -C 4 acyl, phenyl or substituted phenyl, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 2 -C 4 acyl or trifluoromethyl; R 2 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, trifluoromethyl, amino or substituted amino, wherein said substituted amino is substituted either singularly or in combination with C 1 -C 3 alkyl, C 2 -C 4 acyl, phenyl or substituted phenyl, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl; and R 3 is hydrogen, C 2 -C 4 acyl, benzoyl, substituted benzoyl, C 1 -C 4 alkyl, substituted C 1 -C 4 alkyl or allyl, wherein said substituted benzoyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl, and said substituted alkyl is substituted either singularly or in combination with halogen, phenyl, substituted phenyl, amino or substituted amino, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl, and said substituted amino is substituted either singularly or in combination with C 1 -C 3 alkyl, C 1 -C 5 cycloalkyl, phenyl or substituted phenyl, wherein said substituted phenyl is substituted with halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C 2 -C 4 acyl and their salts.
Claim 3
Dependent Claim
47 words
The compound of claim 1 wherein R 1 is C 1 -C 3 alkyl, thiol, amino or substituted amino; R 2 is hydrogen or halogen; and R 3 is hydrogen, C 2 -C 4 acyl, C 1 -C 4 alkyl or substituted C 1 -C 4 alkyl.
Claim 4
Dependent Claim
18 words
The compound of claim 1 selected from the group consisting of6-acetyl-4-(4-chlorophenyl)-2-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, 6-acetyl-4-(4-fluorophenyl)-2-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine monohydrochloride monohydrate and 6-acetyl-2-methyl-4-(4-methylphenyl) -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine monohydrate.
Claim 5
Dependent Claim
11 words
The compound of claim 1 wherein said compound is 6-acetyl-4-(4-chlorophenyl)-5,6,7,8-tetra-hydro-2thiopyrido[4,3-d]pyrimidine monohydrate.
Claim 6
Dependent Claim
19 words
The compound of claim 1 selected from the group consisting of 4-(4-chlorophenyl)-2-(4-trifluoromethylphenylamino) -5,6,7,8-tetrahydropyrido[4,3d]pyrimidine monohydrochloride and 4-(4-chlorophenyl) -6-ethyl-2-(4-trifluromethylphenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride monohydrate.
Claim 7
Dependent Claim
24 words
The compound of claim 1 selected from the group consisting of 6-acetyl-4-(4-chlorophenyl)-2-ethylamino -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, 6- acetyl-4-(4-fluorophenyl)-2-ethylamino-5,6,7,8tetrahydropyrido[4,3-d]pyrimidine, 4-(4-chlorophenyl) -2-ethylamino-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hemihydrate, 6-allyl-4-(4-chlorophenyl) -2-ethylamino-5,6,7,8-tetrahydropyrido[4,3d]pyrimidine, 4-4-chlorophenyl)-6-ethyl-2-ethylamino-5,6,7,8tetrahydropyrido[4,3-d]pyrimidine and2-ethylamino- 4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine monohydrochloride.
Claim 8
Dependent Claim
47 words
The compound of claim 1 selected from the group consisting of 6-acetyl-2-amino-4-(4-chlorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, 6-acetyl-2-amino-4-(4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine monohydrate, 2-amino-4-(4-chlorophenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride, 2-amino-4-(4-fluorophenyl) -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride hemihydrate, 2-amino-4-(4-chlorophenyl) -6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d] pyrimidine dihydrochloride, 2-amino-4-(4-fluorophenyl) -6-ethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine, 2-amino-4-(4-chlorophenyl)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride 1/4 hydrate, 6-allyl-2-amino-4-(4-chlorophenyl) -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride, 6-allyl-2-amino-4-(4-fluorophenyl) -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine dihydrochloride, 2-amino-4-(4-chlorophenyl)-6-methyl -5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine 1/4 hydrate, 6-acetyl-2-amino-4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine monohydrate, 2-amino-6-(2-diethylaminoethyl)-4-(4-fluorophenyl)-5,6,7,8tetrahydropyrido-[4,3-d]pyrimidine trihydrochloride and 2-amino-4-(4-fluorophenyl)-5,6,7,8-tetrahydro-6-(3-dimethylaminopropyl)pyrido[4,3-d]pyrimidine trihydrochloride.
Claim 9
Dependent Claim
11 words
The compound of claim 1 wherein said compound is 6-acetyl-5,6,7,8-tetrahydro-4-(4-methylphenyl)-2-dipropylaminopyrido[4,3-d]pyrimidine monohydrate.
Claim 10
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 1, and a suitable pharmaceutical carrier.
Claim 11
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 2, and a suitable pharmaceutical carrier.
Claim 12
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 3, and a suitable pharmaceutical carrier.
Claim 13
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 4, and a suitable pharmaceutical carrier.
Claim 14
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 5, and a suitable pharmaceutical carrier.
Claim 15
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 6, and a suitable pharmaceutical carrier.
Claim 16
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 7, and a suitable pharmaceutical carrier.
Claim 17
Dependent Claim
27 words
A pharmaceutical composition useful in treating gastrointestinal diseases comprising as an active ingredient an effective amount of the compound of claim 8, and a suitable pharmaceutical carrier.
Claim 18
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 1.
Claim 19
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 2.
Claim 20
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 3.
Claim 21
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 4.
Claim 22
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 5.
Claim 23
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 6.
Claim 24
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 7.
Claim 25
Dependent Claim
19 words
A method of treating gastrointestinal diseases in mammals by administering an effective amount of a compound of claim 8.
References Cited (Backward Citations)
GB1033384A
Cited
US4500525A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-08-11 | 1996-02-10 | 1996-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-08-11 | 2000-02-10 | 2000-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-08-11 | 2004-02-10 | 2004-08-11 | $7700.00 | Window Closed / Lapsed |