US3968115A
Expired / Lapsed
US
⏱️ 0.0 years remaining
1-Alkyl-4-(10 and/or 11)-bromo-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-ylidene piperidine compounds
Assignee: Merck and Co Inc
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Filing: 1972-08-14
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Granted: 1976-07-06
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Expires: 1992-08-14
Abstract
Abstract The new 1-alkyl-4-(10-oxo or -hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine compounds are prepared from the corresponding 10-desoxy compounds having a double bond at the 10,11-position by a process involving bromination, dehydrobromination of the resulting dibromo compound, followed by enamine formation and hydrolysis to give the desired 10-oxo compound. The compounds prepared in this manner are active as antihistamines and as appetite stimulants.
Inventors
- 👤 John D. Prugh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:56
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/68; A; A61; A61K; A61K31/00; A61K31/33; A61K31/395; A61K31/435; A61K31/44; A61K31/445
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
193 words
A compound of the formula ##SPC5## wherein R 1 is lower alkyl; R is methyl or ethyl; n is 0, 1 or 2; X and X' are similar or dissimilar and are selected from hydrogen, an alkyl group having up to 6 carbon atoms, a perfluoroalkyl group having up to 4 carbon atoms, phenyl, amino, an alkylamino group having up to 4 carbon atoms, a dialkylamino group having up to 8 carbon atoms, an alkylsulfonylamino group having up to 4 carbon atoms, halogen (fluorine, chlorine, bromine or iodine), hydroxyl, an alkoxy group having up to 4 carbon atoms, a perfluoroalkoxyl group having up to 4 carbon atoms, cyano, carboxy, carbamoyl, an alkylcarbamoyl group having up to 5 carbon atoms, a dialkylcarbamoyl group having up to 9 carbon atoms, a carbalkoxy group having up to 6 carbon atoms, an alkylmercapto group having up to 4 carbon atoms, a perfluoroalkylmercapto group having up to 4 carbon atoms, an alkylsulfonyl group having up to 4 carbon atoms, a perfluoroalkylsulfonyl group having up to 4 carbon atoms, sulfamoyl, an alkylsulfamoyl group having up to 4 carbon atoms, or a dialkylsulfamoyl group having up to 8 carbon atoms.
Claim 2
Dependent Claim
193 words
A compound of the formula ##SPC5## wherein R 1 is lower alkyl; R is methyl or ethyl; n is 0, 1 or 2; X and X' are similar or dissimilar and are selected from hydrogen, an alkyl group having up to 6 carbon atoms, a perfluoroalkyl group having up to 4 carbon atoms, phenyl, amino, an alkylamino group having up to 4 carbon atoms, a dialkylamino group having up to 8 carbon atoms, an alkylsulfonylamino group having up to 4 carbon atoms, halogen (fluorine, chlorine, bromine or iodine), hydroxyl, an alkoxy group having up to 4 carbon atoms, a perfluoroalkoxyl group having up to 4 carbon atoms, cyano, carboxy, carbamoyl, an alkylcarbamoyl group having up to 5 carbon atoms, a dialkylcarbamoyl group having up to 9 carbon atoms, a carbalkoxy group having up to 6 carbon atoms, an alkylmercapto group having up to 4 carbon atoms, a perfluoroalkylmercapto group having up to 4 carbon atoms, an alkylsulfonyl group having up to 4 carbon atoms, a perfluoroalkylsulfonyl group having up to 4 carbon atoms, sulfamoyl, an alkylsulfamoyl group having up to 4 carbon atoms, or a dialkylsulfamoyl group having up to 8 carbon atoms.
Claim 3
Dependent Claim
6 words
A compound of the formula ##SPC6##
Claim 4
Dependent Claim
6 words
A compound of the formula ##SPC6##
Claim 5
Dependent Claim
21 words
A compound of the formula ##SPC7## wherein X, X', R, R 1 , and n are as defined in claim 1.
Claim 6
Dependent Claim
6 words
A compound of the formula ##SPC8##
Claim 7
Dependent Claim
6 words
A compound of the formula ##SPC8##
Claim 8
Dependent Claim
54 words
The process which comprises treating 1-methyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine with bromine to produce 10,11-dibromo-10,11-dihydro-1-methyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine and subsequently treating said 10,11-dibromo compound with a strong base to produce the corresponding 10-bromo-1-methyl-5-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, treating said 10-bromo compound with piperidine in the presence of a strong base to produce the corresponding 10-enamine compound 1-methyl-4-(10-(1piperidyl)-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, and hydrolyzing said 10-(1-piperidyl)compound to produce 1-methyl-4-(10,11-dihydro-10-oxo-dibenzo[a,d]cyclohepten-5-ylidene piperidine.
Claim 9
Dependent Claim
54 words
The process which comprises treating 1-methyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine with bromine to produce 10,11-dibromo-10,11-dihydro-1-methyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine and subsequently treating said 10,11-dibromo compound with a strong base to produce the corresponding 10-bromo-1-methyl-5-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, treating said 10-bromo compound with piperidine in the presence of a strong base to produce the corresponding 10-enamine compound 1-methyl-4-(10-(1piperidyl)-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine, and hydrolyzing said 10-(1-piperidyl)compound to produce 1-methyl-4-(10,11-dihydro-10-oxo-dibenzo[a,d]cyclohepten-5-ylidene piperidine.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1979-07-06 | 1980-01-05 | 1980-07-06 | $2000.00 | Window Closed / Lapsed |
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