US4031222A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Trifluoromethylthio (and sulfonyl) derivatives of cyproheptadine analogs
Assignee: Merck and Co Inc
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Filing: 1975-12-22
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Granted: 1977-06-21
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Expires: 1995-12-22
Abstract
Abstract Cyproheptadine derivatives substituted with a trifluoromethylthio or trifluoromethylsulfonyl group in one of the benzo rings and having a hydroxyalkyl or cycloalkylalkyl group on the piperidine nitrogen are potent antipsychotic agents, with a low propensity to induce extrapyramidal side effects that are experienced with most major tranquilizers. The tranquilizing activity is predominantly in the levorotatory enantiomers, whereas the dextrorotatory enantiomers have anticholinergic activity. Each enantiomer is useful as a source of the other by racemization. The novel compounds are prepared by treatment of the corresponding iodo or bromo compound with bis(trifluoromethylthio)mercury and copper powder.
Inventors
- 👤 David C. Remy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 00:11
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/38; A; A61; A61P; A61P25/00; A61P25/18; C07D211/40; C07D211/44; C07D211/68; C07D211/70; C07D211/72; C07D211/74; C07D211/76; C07F; C07F3/00; C07F3/02
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
38 words
A compound of structural formula: ##STR10## or a pharmaceutically acceptable salt thereof, wherein R 1 is --SCF 3 or SO 2 CF 3 , R 2 is ##STR11## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 2
Dependent Claim
38 words
A compound of structural formula: ##STR10## or a pharmaceutically acceptable salt thereof, wherein R 1 is --SCF 3 or SO 2 CF 3 , R 2 is ##STR11## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 3
Dependent Claim
14 words
The compound of claim 1 of structural formula: ##STR12## or pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
15 words
The compound of claim 2 or pharmaceutically acceptable salt thereof wherein R 3 is hydrogen.
Claim 5
Dependent Claim
17 words
The compound of claim 3 or pharmaceutically acceptable salt thereof wherein R 1 is --SCF 3 .
Claim 6
Dependent Claim
19 words
The compound of claim 3 or pharmaceutically acceptable salt thereof wherein R 1 is --SO 2 CF 3 .
Claim 7
Dependent Claim
13 words
The compound of claim 4, which is 1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, or pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
17 words
The levorotatory enantiomer of the compound of claim 6 which is (-)-1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, or pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
17 words
The dextrorotatory enantiomer of the compound of claim 6, which is (±)-1-cyclopropylmethyl-4-(3-trifluoromethylthio-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine, or pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
25 words
A levorotatory enantiomer of the compound of structural formula: ##STR13## wherein R 2 is ##STR14## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 11
Dependent Claim
25 words
A levorotatory enantiomer of the compound of structural formula: ##STR13## wherein R 2 is ##STR14## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 12
Dependent Claim
13 words
The levorotatory enantiomer of the compound of claim 9 of structural formula: ##STR15##
Claim 13
Independent Claim
58 words
A method of treating psychoses which comprises the administration to a patient in need of such treatment an effective amount of a compound of structural formula: ##STR16## or pharmaceutically acceptable salt thereof, wherein R 1 is --SCF 3 or SO 2 CF 3 ; R 2 is ##STR17## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 14
Independent Claim
58 words
A method of treating psychoses which comprises the administration to a patient in need of such treatment an effective amount of a compound of structural formula: ##STR16## or pharmaceutically acceptable salt thereof, wherein R 1 is --SCF 3 or SO 2 CF 3 ; R 2 is ##STR17## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 15
Dependent Claim
24 words
The method of claim 11 wherein the compound is the levorotatory enantiomer of the compound of structural formula: ##STR18## or pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
58 words
A pharmaceutical composition in unit dosage form for the treatment of psychoses comprising a carrier and an effective amount of a compound of structural formula: ##STR19## or a pharmaceutically acceptable salt thereof, wherein R 1 is --SCF 3 or SO 2 CF 3 , R 2 is ##STR20## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 17
Dependent Claim
58 words
A pharmaceutical composition in unit dosage form for the treatment of psychoses comprising a carrier and an effective amount of a compound of structural formula: ##STR19## or a pharmaceutically acceptable salt thereof, wherein R 1 is --SCF 3 or SO 2 CF 3 , R 2 is ##STR20## and R 3 is hydrogen, C 1-3 alkyl or fluoro.
Claim 18
Dependent Claim
25 words
The pharmaceutical composition of claim 13, wherein the compound is the levorotatory enantiomer of the compound of structural formula: ##STR21## or pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
13 words
The dextrorotatory enantiomer of the compound of claim 9 of structural formula: ##STR22##
References Cited (Backward Citations)
US3851059A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-06-20 | 1980-12-20 | 1981-06-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-06-20 | 1984-12-20 | 1985-06-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-06-20 | 1988-12-20 | 1989-06-21 | $7700.00 | Window Closed / Lapsed |