US4450162A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Pyrimidine derivatives and a pharmaceutical composition containing them
Assignee: Sankyo Co Ltd
•
Filing: 1982-06-02
•
Granted: 1984-05-22
•
Expires: 2002-06-02
Abstract
Abstract New 4-anilinopyrimidine derivatives of formula (I): <IMAGE> (I) (wherein: R1 and R2 are the same or different and each represents a C1-C6 alkyl group or R1 and R2 together represent a C3-C5 alkylene group; R3 represents a hydrogen atom or a C1-C6 alkyl group; n is 0, 1 or 2; and R4 represents a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group, a halogen atom, a nitro group, a C1-C6 alkanesulphonyl group, a cyano group, a carboxy group or a C2-C7 alkoxycarbonyl group and, when n is 2, the two groups represented by R4 may be the same or different or they may together represent a methylenedioxy group) and pharmaceutically acceptable acid addition salts thereof have been found to have strong antidepressant activity, with low toxicity and very few side-effects. The compounds may be formulated in conventional pharmaceutical compositions for administration by various routes and may be prepared by reacting a 4-halopyrimidine with aniline or an aniline derivative.
Inventors
- 👤 Toshiharu Kamioka
- 👤 Isao Nakayama
- 👤 Takeo Honda
- 👤 Takashi Kobayashi
- 👤 Tokio Obata
- 👤 Katsutoshi Fujii
- 👤 Mikio Kojima
- 👤 Yuji Akiyoshi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 16:12
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; A; A61; A61P; A61P25/00; A61P25/24; A61P25/26; C07D239/70
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
146 words
Compounds of formula (I): ##STR8## (wherein: R 1 and R 2 are the same or different and each represents a C 1 -C 6 alkyl group or R 1 and R 2 together represent a C 3 -C 5 alkylene group; R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group; n is 0, 1 or 2; and R 4 represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, a halogen atom, a nitro group, a C 1 -C 6 alkanesulphonyl group, a cyano group, a carboxy group or a C 2 -C 7 alkoxycarbonyl group and, when n is 2, the two groups represented by R 4 may be the same or different or they may together represent a methylenedioxy group) and pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
146 words
Compounds of formula (I): ##STR8## (wherein: R 1 and R 2 are the same or different and each represents a C 1 -C 6 alkyl group or R 1 and R 2 together represent a C 3 -C 5 alkylene group; R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group; n is 0, 1 or 2; and R 4 represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, a halogen atom, a nitro group, a C 1 -C 6 alkanesulphonyl group, a cyano group, a carboxy group or a C 2 -C 7 alkoxycarbonyl group and, when n is 2, the two groups represented by R 4 may be the same or different or they may together represent a methylenedioxy group) and pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
146 words
Compounds as claimed in claim 1, wherein: R 1 and R 2 are the same or different and each represents an alkyl group having from 1 to 4 carbon atoms or R 1 and R 2 together represent an alkylene group having 3 or 4 carbon atoms; R 3 represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; n is 0, 1 or 2; and R 4 represents an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, a trifluoromethyl group, a halogen atom, a nitro group, an alkanesulphonyl group having from 1 to 3 carbon atoms, a cyano group, a carboxy group or an alkoxycarbonyl group having from 2 to 4 carbon atoms or, when n is 2, the two symbols R 4 may together represent a methylenedioxy group.
Claim 4
Dependent Claim
134 words
Compounds as claimed in claim 1, wherein: R 1 represents a methyl group, an ethyl group or a butyl group and R 2 represents a methyl group, or R 1 and R 2 together represent a trimethylene group; R 3 represents a hydrogen atom; n is 0, 1 or 2; and when n is 1, R 4 is at the 4-position of the benzene ring and represents an ethyl group, an isopropyl group, a trifluoromethyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, a methanesulphonyl group, a cyano group, a carboxy group, a methoxycarbonyl group or an ethoxycarbonyl group, or when n is 2, the two symbols R 4 are at the 3 and 4 positions of the benzene ring and each represents a chlorine atom.
Claim 5
Dependent Claim
91 words
Compounds as claimed in claim 1, wherein: R 1 represents a methyl group, an ethyl group or a butyl group and R 2 represents a methyl group, or R 1 and R 2 together represent a trimethylene group; R 3 represents a hydrogen atom; n is 0 or 1; and when n is 1, R 4 is at the 4-position of the benzene ring and represents an ethyl group, an isopropyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a cyano group or a methanesulphonyl group.
Claim 6
Dependent Claim
8 words
4-(4-Cyanoanilino)-6,7-dihydro-5H-cyclopenta[d]pyrimidine and pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
8 words
4-(4-Cyanoanilino)-6,7-dihydro-5H-cyclopenta[d]pyrimidine and pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
8 words
4-(4-Bromoanilino)-5,6-dimethylpyrimidine and pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
8 words
4-(4-Bromoanilino)-5,6-dimethylpyrimidine and pharmaceutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim
8 words
4-(4-Bromoanilino)-5-n-butyl-6-methylpyrimidine and pharmaceutically acceptable acid addition salts thereof.
Claim 11
Dependent Claim
8 words
4-(4-Bromoanilino)-5-n-butyl-6-methylpyrimidine and pharmaceutically acceptable acid addition salts thereof.
Claim 12
Dependent Claim
172 words
A pharmaceutical composition comprising an effective amount of an antidepressant compound in admixture with a pharmaceutically acceptable carrier or diluent, wherein the antidepressant compound is selected from compounds of formula (I): ##STR9## (wherein: R 1 and R 2 are the same or different and each represents a C 1 -C 6 alkyl group or R 1 and R 2 together represent a C 3 -C 5 alkylene group; R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group; n is 0, 1 or 2; and R 4 represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, a halogen atom, a nitro group, a C 1 -C 6 alkanesulphonyl group, a cyano group, a carboxy group or a C 2 -C 7 alkoxycarbonyl group and, when n is 2, the two groups represented by R 4 may be the same or different or they may together represent a methylenedioxy group) and pharmaceutically acid addition salts thereof.
Claim 13
Dependent Claim
172 words
A pharmaceutical composition comprising an effective amount of an antidepressant compound in admixture with a pharmaceutically acceptable carrier or diluent, wherein the antidepressant compound is selected from compounds of formula (I): ##STR9## (wherein: R 1 and R 2 are the same or different and each represents a C 1 -C 6 alkyl group or R 1 and R 2 together represent a C 3 -C 5 alkylene group; R 3 represents a hydrogen atom or a C 1 -C 6 alkyl group; n is 0, 1 or 2; and R 4 represents a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 haloalkyl group, a halogen atom, a nitro group, a C 1 -C 6 alkanesulphonyl group, a cyano group, a carboxy group or a C 2 -C 7 alkoxycarbonyl group and, when n is 2, the two groups represented by R 4 may be the same or different or they may together represent a methylenedioxy group) and pharmaceutically acid addition salts thereof.
Claim 14
Dependent Claim
21 words
A composition as claimed in claim 8, wherein said antidepressant compound is 4-(4-cyanoanilino)-6,7-dihydro-5Hcyclopenta[d]pyrimidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 15
Dependent Claim
21 words
A composition as claimed in claim 8, wherein said antidepressant compound is 4-(4-bromoanilino)-5,6-dimethylpyrimidine or a pharmaceutically acceptable acid addition salt thereof.
Claim 16
Dependent Claim
21 words
A composition as claimed in claim 8, wherein said antidepressant compound is 4-(4-bromoanilino)-5-n-butyl-6-methylpyrimidine or a pharmaceutically acceptable acid addition salt thereof.
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) | 1987-05-22 | 1987-11-21 | 1988-05-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-22 | 1991-11-21 | 1992-05-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-22 | 1995-11-21 | 1996-05-22 | $7700.00 | Window Closed / Lapsed |