US3947449A
Expired / Lapsed
US
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Tetrahydroacridones having chemotherapeutic action and process for preparing them
Assignee: Hoechst AG
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Filing: 1974-07-22
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Granted: 1976-03-30
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Expires: 1994-07-22
Abstract
Abstract Tetrahydroacridones and their salts with physiologically tolerated acids and bases and process for preparing them. The compounds have a valuable chemotherapeutic action and may be used as drugs against protozoan diseases.
Inventors
- 👤 Walter Durckheimer
- 👤 Wolfgang Raether
- 👤 Hubert Georg Seliger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 16:00
CPC Classifications
C; C07; C07D; C07D219/00; C07D219/04; C07D219/06; A; A61; A61P; A61P33/00; A61P33/02; C07D219/08
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
106 words
A tetrahydroacridone of the formula ##SPC4## and salts thereof with physiologically tolerated acids and bases, wherein R 1 is oxygen; R 2 - R 7 , which may be the same or different are hydrogen, straight-chain or branched lower alkyl having 1 to 4 carbon atoms, phenyl, or phenyl mono- or di-substituted with fluorine, chlorine, or trifluoromethyl, except that only one of R 2 - R 7 is phenyl or substituted phenyl; R 8 , R 9 , and R 11 , which may be the same or different, are hydrogen, fluorine, chlorine, or trifluoromethyl; R 10 is chlorine; and R 12 is hydrogen or hydroxy.
Claim 2
Dependent Claim
106 words
A tetrahydroacridone of the formula ##SPC4## and salts thereof with physiologically tolerated acids and bases, wherein R 1 is oxygen; R 2 - R 7 , which may be the same or different are hydrogen, straight-chain or branched lower alkyl having 1 to 4 carbon atoms, phenyl, or phenyl mono- or di-substituted with fluorine, chlorine, or trifluoromethyl, except that only one of R 2 - R 7 is phenyl or substituted phenyl; R 8 , R 9 , and R 11 , which may be the same or different, are hydrogen, fluorine, chlorine, or trifluoromethyl; R 10 is chlorine; and R 12 is hydrogen or hydroxy.
Claim 3
Dependent Claim
2 words
7-chloro-3-(2-chloro-4-trifluoromethylphenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 4
Dependent Claim
2 words
7-chloro-3-(2-chloro-4-trifluoromethylphenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 5
Dependent Claim
2 words
7-chloro-10-hydroxy-1-oxo-3-phenyl-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 6
Dependent Claim
2 words
7-chloro-10-hydroxy-1-oxo-3-phenyl-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 7
Dependent Claim
2 words
7-chloro-3-(4-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 8
Dependent Claim
2 words
7-chloro-3-(4-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 9
Dependent Claim
2 words
7-chloro-3-(2-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 10
Dependent Claim
2 words
7-chloro-3-(2-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 11
Dependent Claim
2 words
7-chloro-10-hydroxy-1-oxo-3-(4-trifluoromethylphenyl)-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 12
Dependent Claim
2 words
7-chloro-10-hydroxy-1-oxo-3-(4-trifluoromethylphenyl)-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 13
Dependent Claim
2 words
7-chloro-3-(2,4-dichlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 14
Dependent Claim
2 words
7-chloro-3-(2,4-dichlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 15
Dependent Claim
2 words
7-chloro-3-(3-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 16
Dependent Claim
2 words
7-chloro-3-(3-chlorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 17
Dependent Claim
2 words
7-chloro-3-(4-fluorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 18
Dependent Claim
2 words
7-chloro-3-(4-fluorophenyl)-10-hydroxy-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 19
Dependent Claim
2 words
7-chloro-10-hydroxy-3-(4-nitrophenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 20
Dependent Claim
2 words
7-chloro-10-hydroxy-3-(4-nitrophenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 21
Dependent Claim
2 words
7-chloro-10-hydroxy-3-(2-methoxyphenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 22
Dependent Claim
2 words
7-chloro-10-hydroxy-3-(2-methoxyphenyl)-1-oxo-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 23
Dependent Claim
2 words
6,7-dichloro-10-hydroxy-1-oxo-3-(3-trifluorophenyl)-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 24
Dependent Claim
2 words
6,7-dichloro-10-hydroxy-1-oxo-3-(3-trifluorophenyl)-1,2,3,4-tetrahydro-9 (10H)-acridone.
Claim 25
Independent Claim
153 words
A method for making a tetrahydroacridone of the formula ##SPC5## wherein R 2 - R 7 , which may be the same or different, are hydrogen, straight-chain or branched lower alkyl having 1 to 4 carbon atoms, phenyl, nitrophenyl, lower alkoxy phenyl having 1 to 4 carbon atoms in the alkoxy, methylenedioxy phenyl, sulfamyl phenyl, or phenyl mono- or di-substituted with fluoro, chloro, or trifluoromethyl, except that only one of R 2 - R 7 is phenyl or substituted phenyl; and R 8 - R 11 , which may be the same or different, are hydrogen, fluorine, chlorine, bromine, lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, or trifluoromethyl, except that R 10 is other than hydrogen; which comprises reacting a compound of the formula ##SPC6## with a compound of the formula ##SPC7## in a water-miscible solvent and in the presence of a mineral acid.
Claim 26
Independent Claim
153 words
A method for making a tetrahydroacridone of the formula ##SPC5## wherein R 2 - R 7 , which may be the same or different, are hydrogen, straight-chain or branched lower alkyl having 1 to 4 carbon atoms, phenyl, nitrophenyl, lower alkoxy phenyl having 1 to 4 carbon atoms in the alkoxy, methylenedioxy phenyl, sulfamyl phenyl, or phenyl mono- or di-substituted with fluoro, chloro, or trifluoromethyl, except that only one of R 2 - R 7 is phenyl or substituted phenyl; and R 8 - R 11 , which may be the same or different, are hydrogen, fluorine, chlorine, bromine, lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, or trifluoromethyl, except that R 10 is other than hydrogen; which comprises reacting a compound of the formula ##SPC6## with a compound of the formula ##SPC7## in a water-miscible solvent and in the presence of a mineral acid.
Claim 27
Dependent Claim
21 words
A method as in claim 13 wherein said tetrahydroacridone is subsequently reacted with hydrazine to replace the 1-oxygen atom by 1-hydrazono.
Claim 28
Dependent Claim
22 words
A method as in claim 13 wherein said tetrahydroacridone is subsequently reacted with phosphorus trichloride to reduce the 10-hydroxy group to hydrogen.
Claim 29
Dependent Claim
45 words
A method as in claim 13 wherein said tetrahydroacridone is subsequently reacted with an acid chloride or acid anhydride of the formula R.sup.13 --COCl or R.sup.13 --CO--O--CO--R.sup.13 , wherein R 13 is lower alkyl having 1 to 4 carbon atoms, to esterify the 10-hydroxy group.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-03-30 | 1979-09-29 | 1980-03-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-03-30 | 1983-09-29 | 1984-03-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-03-30 | 1987-09-29 | 1988-03-30 | $7700.00 | Window Closed / Lapsed |