US4366154A
Expired / Lapsed
US
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Tropyl derivatives
Assignee: Sandoz Inc
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Filing: 1981-11-09
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Granted: 1982-12-28
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Expires: 2001-11-09
Abstract
Abstract Tropyl derivatives of the formula: <IMAGE> in which R1 is (a) phenyl linked through a direct bond, -O-, <IMAGE> (in which m=2 or 3); (b) diphenylmethyl; or (c) 10H-phenothiazin-10-yl; (each of which type may be substituted, or unsubstituted); R2 is -H, -OH, or -O Si (CH3)3; and R3 is substituted or unsubstituted phenyl, e.g. 4-[3-(4-fluorobenzoyl)-8-azabicyclo [3.2.1]oct-8-yl]-1-(-4-fluorophenyl)-1-butanone, in free base form or pharmaceutically acceptable acid addition salts are useful as pharmaceuticals.
Inventors
- 👤 John C. Tomesch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:51
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07D451/04; C07D451/06; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
203 words
A compound which is a free base of the formula: ##STR23## wherein each of X and Y is independently, a hydrogen atom, fluoro, chloro or bromo, alkyl or alkoxy having from 1 to 4 carbon atoms, or trifluoromethyl, provided that when X and Y are trifluoromethyl, branched alkyl, or branched alkoxy, they are not on adjacent carbon atoms; n is a whole number of from 1 to 4; R 1 is of type; (a) a radical of the formula: ##STR24## wherein each of X' and Y' is independently, a hydrogen atom, fluoro, chloro or bromo; alkyl or alkoxy having from 1 to 4 carbon atoms, or trifluoromethyl, provided that when X' and Y' are trifluoromethyl, branched alkyl or branched alkoxy they are not on adjacent carbon atoms, and Z is ##STR25## (c) --O--; or (d) a direct bond, wherein m is 2 or 3; (b) a radical of the formula: ##STR26## in which X a and Y a are, independently, a hydrogen atom or fluoro; or (c) a radical of the formula: ##STR27## in which X' is defined above; and, R 2 is (a) a hydrogen atom; (b) --OH; or (c) --O--Si(CH 3 ) 3 ; or a non-toxic acid addition salt thereof.
Claim 2
Dependent Claim
203 words
A compound which is a free base of the formula: ##STR23## wherein each of X and Y is independently, a hydrogen atom, fluoro, chloro or bromo, alkyl or alkoxy having from 1 to 4 carbon atoms, or trifluoromethyl, provided that when X and Y are trifluoromethyl, branched alkyl, or branched alkoxy, they are not on adjacent carbon atoms; n is a whole number of from 1 to 4; R 1 is of type; (a) a radical of the formula: ##STR24## wherein each of X' and Y' is independently, a hydrogen atom, fluoro, chloro or bromo; alkyl or alkoxy having from 1 to 4 carbon atoms, or trifluoromethyl, provided that when X' and Y' are trifluoromethyl, branched alkyl or branched alkoxy they are not on adjacent carbon atoms, and Z is ##STR25## (c) --O--; or (d) a direct bond, wherein m is 2 or 3; (b) a radical of the formula: ##STR26## in which X a and Y a are, independently, a hydrogen atom or fluoro; or (c) a radical of the formula: ##STR27## in which X' is defined above; and, R 2 is (a) a hydrogen atom; (b) --OH; or (c) --O--Si(CH 3 ) 3 ; or a non-toxic acid addition salt thereof.
Claim 3
Dependent Claim
13 words
A compound of claim 1 in which R 1 is of type (a).
Claim 4
Dependent Claim
13 words
A compound of claim 1 in which R 1 is of type (b).
Claim 5
Dependent Claim
13 words
A compound of claim 1 in which R 1 is of type (c).
Claim 6
Dependent Claim
16 words
A compound of claim 2, 3 or 4 in which R 2 is of type (a).
Claim 7
Dependent Claim
16 words
A compound of claim 2, 3 or 4 in which R 2 is of type (b).
Claim 8
Dependent Claim
16 words
A compound of claim 2, 3 or 4 in which R 2 is of type (c).
Claim 9
Dependent Claim
17 words
A compound of claim 2 or 3 in which R 2 is of type (a) or (b).
Claim 10
Dependent Claim
15 words
A compound of claim 4 in which R 2 is of type (a) or (b).
Claim 11
Dependent Claim
9 words
The compound of claim 2 which is 4-[3-(4-fluorobenzoyl)-8-azabicyclo[3.2.1]oct-8-yl]-1-(4-fluorophenyl)-1-butanone (B-form).
Claim 12
Dependent Claim
10 words
The compound of claim 2 which is (8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)4-fluorophenyl methanone (B-form).
Claim 13
Dependent Claim
11 words
The compound of claim 3 which is {8-[4,4-bis(4-fluorophenyl)butyl]-3-hydroxy 8-azabicyclo[3.2.1]oct-3-yl}phenyl methanone (B-form).
Claim 14
Dependent Claim
9 words
The compound of claim 3 which is {8-[3-(4-methoxyphenoxy)propyl]-3-hydroxy-8-azabicyclo[3.2.1]oct-3-yl}(4-fluorophenyl)methanone (B-form).
Claim 15
Dependent Claim
10 words
The compound of claim 7 which is {8-[4,4-bis(4-fluorophenyl)butyl]3-trimethylsiloxy-8-azabicyclo[3.2.1]oct-3-yl}phenyl methanone (B-form).
Claim 16
Dependent Claim
10 words
The compound of claim 7 which is ((8-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-3-trimethylsiloxy-8-azabicyclo[3.2.1]oct-3-yl))phenyl methanone (B-form).
Claim 17
Dependent Claim
10 words
The compound of claim 4 which is 8[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-8-azabicyclo[3.2.1]oct-3-yl]phenyl methanone (B-form).
Claim 18
Dependent Claim
9 words
The compound of claim 4 which is {8-[3-(2-chloro-10H-phenothiazin-10-yl)propyl]-3-hydroxy-8-azabicyclo[3.2.1]oct-3-yl}(4-fluorophenyl)methanone (B-form).
Claim 19
Dependent Claim
20 words
A method of tranquillizing a mammal comprising administering to a mammal a anti-psychotic-effective amount of a compound of claim 1.
Claim 20
Dependent Claim
22 words
A pharmaceutical composition comprising in unit dose form an inert pharmaceutically-acceptable carrier and a anti-psychotic-effective amount of a compound of claim 1.
References Cited (Backward Citations)
US2800476A
Cited
US3987042A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-12-27 | 1986-06-28 | 1986-12-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-12-27 | 1990-06-28 | 1990-12-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-12-27 | 1994-06-28 | 1994-12-28 | $7700.00 | Window Closed / Lapsed |