US4532240A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Diaminopyrimidines
Assignee: Warner Lambert Co LLC
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Filing: 1983-08-09
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Granted: 1985-07-30
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Expires: 2003-08-09
Abstract
Abstract Substituted-phenyl derivatives of 5-(1,4-piperazinyl)-2,4-pyrimidinediamine are effective as antibacterial and antitumor agents. Methods of preparing such compounds, pharmaceutical compositions based thereon, and a method of treating bacterial infections in a mammal in need of such treatment are disclosed.
Inventors
- 👤 Leslie M. Werbel
- 👤 Jocelyn H. Hung
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 08:53
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; C07D239/46; C07D239/50; C07D239/52; C07D239/54; C07D239/545; C07D239/553
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
333 words
A compound having the structural formula I ##STR25## where A. R 1 is hydrogen or alkyl of from one to six carbon atoms; B. R 2 and R 3 are independently hydrogen or methyl; C. R 4 and R 5 are independently: (1) hydrogen; (2) halogen; (3) nitro; (4) cyano; (5) trifluoromethyl; (6) hydroxyl; (7) alkyl of from one to six carbon atoms; (8) alkoxyl of from one to six carbon atoms; (9) alkanoyl of from one to six carbon atoms; (10) --NR 6 R 7 , where R 6 and R 7 are independently (a) hydrogen, (b) alkyl of from one to six carbon atoms, (c) alkanoyl of from one to six carbon atoms; (11) --COOR 8 where R 8 is (a) hydrogen, (b) a pharmaceutically acceptable metal cation, (c) a pharmaceutically acceptable amine cation, (d) alkyl of from one to six carbon atoms; (12) --CONR 9 R 10 where R 9 and R 10 are independently (a) hydrogen, (b) alkyl of from one to six carbon atoms, (c) alkyl of from one to six carbon atoms, substituted with one or two carboxyl groups, (d) alkyl of from one to six carbon atoms, substituted with one to two carboxyl groups and one --OH, --SH, or --NH 2 group, (e) alkyl of from one to six carbon atoms, substituted with one or two carboalkoxy groups of from one to six carbon atoms, (f) alkyl of from one to six carbon atoms, substituted with one or two carboalkoxy groups of from one to six carbon atoms and one --OH, --SH, or --NH 2 group; (13) ##STR26## where R 11 is hydrogen, or alkyl of from one to six carbon atoms; or (14) --SO 2 R 12 where R 12 is (a) hydroxyl, (b) alkyl of from one to six carbon atoms, (c) alkoxy of from one to six carbon atoms, or (d) --NHR 13 where R 13 is hydrogen or alkyl of from one to six carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
333 words
A compound having the structural formula I ##STR25## where A. R 1 is hydrogen or alkyl of from one to six carbon atoms; B. R 2 and R 3 are independently hydrogen or methyl; C. R 4 and R 5 are independently: (1) hydrogen; (2) halogen; (3) nitro; (4) cyano; (5) trifluoromethyl; (6) hydroxyl; (7) alkyl of from one to six carbon atoms; (8) alkoxyl of from one to six carbon atoms; (9) alkanoyl of from one to six carbon atoms; (10) --NR 6 R 7 , where R 6 and R 7 are independently (a) hydrogen, (b) alkyl of from one to six carbon atoms, (c) alkanoyl of from one to six carbon atoms; (11) --COOR 8 where R 8 is (a) hydrogen, (b) a pharmaceutically acceptable metal cation, (c) a pharmaceutically acceptable amine cation, (d) alkyl of from one to six carbon atoms; (12) --CONR 9 R 10 where R 9 and R 10 are independently (a) hydrogen, (b) alkyl of from one to six carbon atoms, (c) alkyl of from one to six carbon atoms, substituted with one or two carboxyl groups, (d) alkyl of from one to six carbon atoms, substituted with one to two carboxyl groups and one --OH, --SH, or --NH 2 group, (e) alkyl of from one to six carbon atoms, substituted with one or two carboalkoxy groups of from one to six carbon atoms, (f) alkyl of from one to six carbon atoms, substituted with one or two carboalkoxy groups of from one to six carbon atoms and one --OH, --SH, or --NH 2 group; (13) ##STR26## where R 11 is hydrogen, or alkyl of from one to six carbon atoms; or (14) --SO 2 R 12 where R 12 is (a) hydroxyl, (b) alkyl of from one to six carbon atoms, (c) alkoxy of from one to six carbon atoms, or (d) --NHR 13 where R 13 is hydrogen or alkyl of from one to six carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
249 words
A compound in accordance with claim 1 wherein R 4 and R 5 are independently A. nitro; B. cyano; C. trifluoromethyl; D. alkanoyl of from one to six carbon atoms; E. --COOR 8 where R 8 is (1) hydrogen, (2) a pharmaceutically acceptable metal cation, (3) a pharmaceutically acceptable amine cation, or (4) alkyl of from one to six carbon atoms; F. --CONR 9 R 10 where R 9 and R 10 are independently (1) hydrogen, (2) alkyl of from one to six carbon atoms, (3) alkyl of from one to six carbon atoms, substituted with one or two carboxyl groups, (4) alkyl of from one to six carbon atoms, substituted with one or two carboxyl group and one --OH, --SH, or --NH 2 group, (5) alkyl of from one to six carbon atoms, substituted with one or two carboalkoxy groups of from one to six carbon atoms (6) alkyl of from one to six carbon atoms, substituted with one or two carboalkoxy groups of from one to six carbon atoms and one --OH, --SH, or --NH 2 group; G. ##STR27## where R 11 is hydrogen or alkyl of from one to six carbon atoms; or H. --SO 2 R 12 where R 12 is (1) hydroxyl, (2) alkyl of from one to six carbon atoms, (3) alkoxy of from one to six carbon atoms, or (4) --NHR 13 where R 13 is hydrogen or alkyl of from one to six carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
80 words
A compound in accordance with claim 1 wherein R 4 and R 5 are independently A. hydrogen; B. halogen; C. hydroxyl; D. alkyl of from one to six carbon atoms; E. alkoxyl of from one to six carbon atoms; or F. --NR 6 R 7 , where R 6 and R 7 are independently (1) hydrogen, (2) alkyl of from one to six carbon atoms, (3) alkanoyl of from one to six carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
20 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid ethyl ester and the pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 5-[4-(4-cyanophenyl)-1-piperazinyl]-6-methyl-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
18 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]-benzoyl]-L-glutamic acid and the pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
19 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]-benzoyl]-L-glutamic acid diethyl ester and the pharmaceutically acceptable salts
Claim 10
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 6-methyl-5-[4-(4-nitrophenyl)-1-piperazinyl]-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 5-[4-(4-acetylphenyl)-1-piperazinyl]-6-methyl-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 12
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-diamino-6-methyl-pyrimidinyl)-1-piperazinyl]-N-methyl benzamide and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
17 words
A compound in accordance with claim 1 having the name [4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]glycine and the pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
19 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]glycine methyl ester and the pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 6-methyl-5-[4-[4-(methylsulfonyl)phenyl]-1-piperazinyl]-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 16
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 5-[4-(4-cyanophenyl)-1-piperazinyl]-6-ethyl-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-diamino-6-ethyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid and the pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim
18 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-ethyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid and the pharmaceutically acceptable salts thereof.
Claim 19
Dependent Claim
20 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-ethyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid diethyl ester, and the pharmaceutically acceptable salts thereof.
Claim 20
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 5-[4-(4-cyanophenyl)-1-piperazinyl]-6-propyl-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 21
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid and the pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
18 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid and the pharmaceutically acceptable salts thereof.
Claim 23
Dependent Claim
20 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-L-glutamic acid diethyl ester and the pharmaceutically acceptable salts thereof.
Claim 24
Dependent Claim
20 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-diamino-6-propyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid ethyl ester and the pharmaceutically acceptable salts thereof.
Claim 25
Dependent Claim
18 words
A compound in accordance with claim 1 having the name 6-methyl-5-(4-phenyl-1-piperazinyl)-2,4-pyrimidinediamine, hydrochloride and the pharmaceutically acceptable salts thereof.
Claim 26
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 5-[4-(4-chlorophenyl)-1-piperazinyl]-6-methyl-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 27
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 5-[4-(4-aminophenyl-1-piperazinyl]-6-methyl-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 28
Dependent Claim
17 words
A compound in accordance with claim 1 having the name N-[4-[4-(2,4-Diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoyl]-glycine and the pharmaceutically acceptable salts thereof.
Claim 29
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 4-[4-(2,4-Diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]-N,N-dimethylbenzenesulfonamide and the pharmaceutically acceptable salts thereof.
Claim 30
Dependent Claim
17 words
A compound in accordance with claim 1 having the name 6-Methyl-5-[4-[4-trifluoromethyl)phenyl]-1-piperazinyl]-2,4-pyrimidinediamine and the pharmaceutically acceptable salts thereof.
Claim 31
Dependent Claim
33 words
A compound having structural formula II ##STR28## wherein R 1 is hydrogen or alkyl of from one to six carbon atoms and wherein R 2 and R 3 are independently hydrogen or methyl.
Claim 32
Dependent Claim
33 words
A compound having structural formula II ##STR28## wherein R 1 is hydrogen or alkyl of from one to six carbon atoms and wherein R 2 and R 3 are independently hydrogen or methyl.
Claim 33
Dependent Claim
29 words
A pharmaceutical composition comprising an antibacterially effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof in combination with a pharmaceutically acceptable carrier.
Claim 34
Dependent Claim
28 words
A method for treating bacterial infections in a mammal in need of such treatment by administering an effective amount of a pharmaceutical composition as defined in claim 31.
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) | 1988-07-29 | 1989-01-28 | 1989-07-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-07-29 | 1993-01-28 | 1993-07-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-07-29 | 1997-01-28 | 1997-07-30 | $7700.00 | Window Closed / Lapsed |